Tert-butyl 2-hydroxypyrrolidine-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 2-hydroxypyrrolidine-1-carboxylate
• CAS No.: 84766-91-6
• Molecular Formula: C9H17 N O3
• Molecular Weight: 187.239
• DSSTox Substance ID: DTXSID10518803
• Nikkaji Number: J2.892.853J
• Mol file: 84766-91-6.mol

Synonyms:tert-butyl 2-hydroxypyrrolidine-1-carboxylate;84766-91-6;1-Boc-2-hydroxypyrrolidine;N-BOC PRROLIDIN-2-OL;MFCD09031185;N-BOCPRROLIDIN-2-OL;SCHEMBL559852;DTXSID10518803;2-Hydroxy-1-pyrrolidinecarboxylic Acid 1,1-Dimethylethyl Ester;CS-D0581;AKOS006290080;DS-9136;SY046084;F14813;A864004;TERT-BUTYL 2-HYDROXY-1-PYRROLIDINECARBOXYLATE

Chemical Property of Tert-butyl 2-hydroxypyrrolidine-1-carboxylate

Chemical Property:

• Boiling Point: 273.3±33.0 °C(Predicted)
• PKA: 13.92±0.20(Predicted)
• PSA: 49.77000
• Density: 1.142±0.06 g/cm3(Predicted)
• LogP: 1.27360
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, DCM
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 187.12084340
• Heavy Atom Count: 13
• Complexity: 198

Purity/Quality:

97% ^*data from raw suppliers

2-Hydroxy-1-pyrrolidinecarboxylicAcid1,1-DimethylethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC1O
• Uses: 2-Hydroxy-1-pyrrolidinecarboxylic Acid 1,1-Dimethylethyl Ester is an intermediate in the synthesis of (E)-6-Amino-2-hexenoic Acid (A609990), used in the preparation of anti-collagenase active agent.

Technology Process of Tert-butyl 2-hydroxypyrrolidine-1-carboxylate

There total 6 articles about Tert-butyl 2-hydroxypyrrolidine-1-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

tert-butyl pyrrolidine-1-carboxylate (86953-79-9) → tert-butyl 2-hydroxypyrrolidine-1-carboxylate (84766-91-6)

Guidance literature:

In water; acetonitrile; electrochemical oxydation;

DOI:10.1021/jo00170a037

Reference yield:

tert-butyl pyrrolidine-1-carboxylate (86953-79-9) → tert-butyl 2-hydroxypyrrolidine-1-carboxylate (84766-91-6) + N-Boc-2-[(E)-1-hexenyl]pyrrolidine

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; (E)-1-iodohexene; sec.-butyllithium; triphenylantimony; palladium dichloride; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, -78 deg C, 2.) THF, -78 deg C to room temp., 14 h;

DOI:10.1021/jo970985b

Reference yield:

(E)-1-iodohexene (16644-98-7) + tert-butyl pyrrolidine-1-carboxylate (86953-79-9) → tert-butyl 2-hydroxypyrrolidine-1-carboxylate (84766-91-6) + N-Boc-2-[(E)-1-hexenyl]pyrrolidine

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; triphenylantimony; palladium dichloride; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, -78 deg C, 2.) THF, -78 deg C to room temp., 14 h;

DOI:10.1021/jo970985b

upstream raw materials:

tert-butyl pyrrolidine-1-carboxylate

(E)-1-iodohexene

2-iodohex-1-ene

carbon monoxide

Downstream raw materials:

(E)-(6-tert-butoxycarbonylamino)-2-hexenal

{3-[6-benzyloxy-3-formyl-1-(toluene-4-sulfonyl)-1,2-dihydro-quinolin-2-yl]-propyl}-carbamic acid tert-butyl ester

{3-[6-benzyloxy-4-hydroxy-3-methylene-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-quinolin-2-yl]-propyl}-carbamic acid tert-butyl ester

{3-[6-benzyloxy-3-methylene-4-oxo-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-quinolin-2-yl]-propyl}-carbamic acid tert-butyl ester