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| Other Sizes |
| Targets |
tert-Butyl 3-hydroxypyrrolidine-1-carboxylate does not have a defined biological target as it is a synthetic intermediate rather than a pharmacologically active compound. Its role in medicinal chemistry is to serve as a building block for the construction of drug candidates, particularly HIV-1 protease inhibitors. HIV-1 protease is an enzyme essential for viral replication, and its inhibition is a key strategy in the treatment of HIV/AIDS. The pyrrolidine scaffold provides a rigid, chiral framework that can interact with enzyme active sites. The Boc group protects the amine during synthesis.
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| ln Vitro |
As a chemical intermediate, tert-butyl 3-hydroxypyrrolidine-1-carboxylate exhibits no intrinsic pharmacological activity in vitro. Its utility is demonstrated in the synthesis of pyrrolidinone-containing pseudopeptides and HIV-1 protease inhibitors. The compound is used as a building block in medicinal chemistry for the preparation of various bioactive molecules. In cell-based assays, the compound itself is not tested for biological activity. Instead, the products synthesized from this reagent are evaluated for their pharmacological properties. The compound is used exclusively as a chemical intermediate in organic synthesis.
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| ln Vivo |
tert-Butyl 3-hydroxypyrrolidine-1-carboxylate does not exhibit in vivo biological activity as it is not a therapeutic agent. The compound is used as an intermediate for the preparation of HIV-1 protease inhibitors and other pharmaceuticals. Any in vivo effects would be associated with the final products synthesized from this intermediate, not with the intermediate itself. The compound is not administered to animals in pharmacological studies and has no known physiological effects. Its role is strictly chemical—providing a versatile pyrrolidine scaffold.
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| Enzyme Assay |
In vitro enzyme assays for tert-butyl 3-hydroxypyrrolidine-1-carboxylate derivatives typically involve HIV-1 protease inhibition studies. A standard protocol uses purified HIV-1 protease incubated with a fluorogenic peptide substrate in the presence of varying concentrations of the test compound. Proteolytic cleavage of the substrate is monitored by fluorescence increase over time. IC₅₀ values are calculated from dose-response curves. For quality control, the compound is characterized by NMR, HPLC, and melting point determination (62.1-62.2°C). Purity is typically ≥98%.
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| Cell Assay |
In vitro cell culture experiments with tert-butyl 3-hydroxypyrrolidine-1-carboxylate derivatives typically involve HIV-infected cells or cell lines expressing HIV-1 protease. Cells are cultured in appropriate media and treated with compounds at concentrations ranging from 0.1-100 µM for 24-72 hours. Antiviral activity is assessed by measuring viral replication (e.g., p24 antigen production) or cell viability. Cytotoxicity is assessed using MTT or CellTiter-Glo assays. The intermediate itself is typically not tested in cellular systems; rather, the final products are evaluated.
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| Animal Protocol |
In vivo animal studies are not conducted with tert-butyl 3-hydroxypyrrolidine-1-carboxylate itself, as it is a research reagent for chemical synthesis. When the compound is used to synthesize HIV-1 protease inhibitors or other drug candidates, those final products undergo standard preclinical evaluation. Typical protocols for drug candidates include pharmacokinetic studies in rodents (oral or intravenous administration, blood sampling for LC-MS/MS analysis), efficacy studies in animal models of HIV infection or other diseases, and toxicology studies. These studies evaluate the safety and efficacy of the final drug molecules.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of tert-butyl 3-hydroxypyrrolidine-1-carboxylate are not characterized as it is not a drug substance. Based on its physicochemical properties (molecular weight 187.24, logP approximately 1.0-1.5), the compound would be expected to have moderate oral bioavailability if administered. The Boc group would likely be cleaved in vivo to release the free amine, which could undergo further metabolism. However, the compound is not intended for human exposure and has not been evaluated in formal pharmacokinetic studies. For drug candidates synthesized from this intermediate, pharmacokinetic properties are determined as part of drug development.
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| Toxicity/Toxicokinetics |
Toxicological data for tert-butyl 3-hydroxypyrrolidine-1-carboxylate are limited as it is a research reagent. Standard laboratory safety precautions should be followed when handling this compound, including the use of gloves, safety glasses, and working in a fume hood. The compound should be stored in a cool, dry place away from moisture and strong oxidizing agents. No acute toxicity data are available. The compound is not intended for drug, household, or other uses.
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| Additional Infomation |
tert-Butyl 3-hydroxypyrrolidine-1-carboxylate is a versatile building block in medicinal chemistry for the synthesis of HIV-1 protease inhibitors and pyrrolidinone-containing pseudopeptides. The Boc protecting group enables selective deprotection after synthesis to reveal the free amine for further functionalization. The hydroxyl group provides a handle for oxidation, esterification, or other transformations. The compound is also known as 1-Boc-3-pyrrolidinol. It has not undergone clinical trials and is not approved as a pharmaceutical. Its mechanism of action is chemical—serving as a precursor for the synthesis of biologically active pyrrolidine derivatives.
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| Molecular Formula |
C9H17NO3
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|---|---|
| Molecular Weight |
187.24
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| Exact Mass |
187.12
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| CAS # |
103057-44-9
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| PubChem CID |
4416939
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
273.3±33.0 °C at 760 mmHg
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| Melting Point |
62.1-62.2ºC
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| Flash Point |
119.1±25.4 °C
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| Vapour Pressure |
0.0±1.3 mmHg at 25°C
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| Index of Refraction |
1.502
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| LogP |
-0.08
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
13
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| Complexity |
198
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C(N1CC(O)CC1)OC(C)(C)C
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| InChi Key |
APCBTRDHCDOPNY-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H17NO3/c1-9(2,3)13-8(12)10-5-4-7(11)6-10/h7,11H,4-6H2,1-3H3
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| Chemical Name |
tert-butyl 3-hydroxypyrrolidine-1-carboxylate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.3407 mL | 26.7037 mL | 53.4074 mL | |
| 5 mM | 1.0681 mL | 5.3407 mL | 10.6815 mL | |
| 10 mM | 0.5341 mL | 2.6704 mL | 5.3407 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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