(2S)-2-benzyl 1-tert-butyl 5-hydroxypyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: (2S)-2-benzyl 1-tert-butyl 5-hydroxypyrrolidine-1,2-dicarboxylate
• CAS No.: 331949-29-2
• Molecular Formula: C17H23NO5
• Molecular Weight: 321.373
• European Community (EC) Number: 608-841-0
• DSSTox Substance ID: DTXSID201131410
• Nikkaji Number: J1.727.115F
• Mol file: 331949-29-2.mol

Synonyms:SCHEMBL1300929;OHBXTJMWVPACKS-LSLKUGRBSA-N;DTXSID201131410;(2S)-2-benzyl 1-tert-butyl 5-hydroxypyrrolidine-1,2-dicarboxylate;331949-29-2;1-(1,1-Dimethylethyl) 2-(phenylmethyl) (2S)-5-hydroxy-1,2-pyrrolidinedicarboxylate

Chemical Property of (2S)-2-benzyl 1-tert-butyl 5-hydroxypyrrolidine-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 1.44E-08mmHg at 25°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 321.15762283
• Heavy Atom Count: 23
• Complexity: 425

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C(CCC1O)C(=O)OCC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N1[C@@H](CCC1O)C(=O)OCC2=CC=CC=C2

Technology Process of (2S)-2-benzyl 1-tert-butyl 5-hydroxypyrrolidine-1,2-dicarboxylate

There total 9 articles about (2S)-2-benzyl 1-tert-butyl 5-hydroxypyrrolidine-1,2-dicarboxylate 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: 99.0%

benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate (113400-36-5,400626-71-3) → benzyl (2S)-N-tert-butoxycarbonyl-5-hydroxypyrrolidine-2-carboxylate (331949-29-2)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1039/b503014e

Reference yield:

benzyl (L)-pyroglutamate (94885-52-6) → benzyl (2S)-N-tert-butoxycarbonyl-5-hydroxypyrrolidine-2-carboxylate (331949-29-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 37.5 g / 4-dimethylaminopyridine / acetonitrile / 3 h / 25 °C

2: 88 percent / LiEt₃BH / tetrahydrofuran / 2 h / -78 °C

With dmap; lithium triethylborohydride; In tetrahydrofuran; acetonitrile;

DOI:10.1021/ol049665m

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → benzyl (2S)-N-tert-butoxycarbonyl-5-hydroxypyrrolidine-2-carboxylate (331949-29-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 37.5 g / 4-dimethylaminopyridine / acetonitrile / 3 h / 25 °C

2: 88 percent / LiEt₃BH / tetrahydrofuran / 2 h / -78 °C

With dmap; lithium triethylborohydride; In tetrahydrofuran; acetonitrile;

DOI:10.1021/ol049665m

upstream raw materials:

benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

di-tert-butyl dicarbonate

benzyl bromide

benzyl (L)-pyroglutamate

Downstream raw materials:

benzyl (2S)-N-tert-butoxycarbonyl-5-methoxypyrrolidine-2-carboxylate

N-(Boc)-(2S,5S)-(5-(tert-butyl)carboxymethyl)proline benzyl ester

(2S,5R)-5-allylpyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

benzyl (2S)-N-tert-butoxycarbonyl-5-allylpyrrolidine-2-carboxylate