tert-butyl (3S,4S)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (3S,4S)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate
• CAS No.: 252574-03-1
• Molecular Formula: C16H24 N2 O3
• Molecular Weight: 292.378
• European Community (EC) Number: 811-546-1
• DSSTox Substance ID: DTXSID20461013
• Nikkaji Number: J1.699.070A
• Wikidata: Q72448633
• Mol file: 252574-03-1.mol

Synonyms:252574-03-1;(3S,4S)-tert-butyl 3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate;(3S,4S)-N-Boc-3-(benzylamino)-4-hydroxypyrrolidine;tert-butyl (3S,4S)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate;138026-89-8;1-pyrrolidinecarboxylic acid, 3-hydroxy-4-[(phenylmethyl)amino]-, 1,1-dimethylethyl ester, (3r,4r)-rel-;trans-tert-Butyl 3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate;SCHEMBL707350;tert-butyl trans-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate;DTXSID20461013;GVYATPKTSSTHKN-KBPBESRZSA-N;MFCD11109734;AKOS016345565;AS-50775;A5114;CS-0005741;P11071;trans-tert-Butyl3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate;tert-butyl (3s, 4s)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate;tert-Butyl(3S,4S)-3-(Benzylamino)-4-hydroxypyrrolidine-1-carboxylate;(3S,4S)-3-benzylamino-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of tert-butyl (3S,4S)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate

Chemical Property:

• Vapor Pressure: 5.77E-08mmHg at 25°C
• Boiling Point: 424.6°C at 760 mmHg
• PKA: 14.24±0.40(Predicted)
• Flash Point: 210.6°C
• PSA: 61.80000
• Density: 1.16
• LogP: 2.08520
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 292.17869263
• Heavy Atom Count: 21
• Complexity: 348

Purity/Quality:

99% ^*data from raw suppliers

tert-Butyl (3S,4S)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate 97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(C(C1)O)NCC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@@H]([C@H](C1)O)NCC2=CC=CC=C2

Technology Process of tert-butyl (3S,4S)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate

There total 8 articles about tert-butyl (3S,4S)-3-(benzylamino)-4-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: 65.0%

(3S,4S)-3-benzylamino-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (+)-mandelic acid salt (252574-04-2) → (3S,4S)-1-tert-butoxycarbonyl-trans-3-benzylamino-4-hydroxypyrrolidine (252574-03-1)

Guidance literature:

With water; potassium carbonate;

Reference yield: 39.0%

tert-butyl (+/-)-trans-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate → (3S,4S)-1-tert-butoxycarbonyl-trans-3-benzylamino-4-hydroxypyrrolidine (252574-03-1)

Guidance literature:

tert-butyl (+/-)-trans-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate; With (+)-mandelic acid; In water; acetonitrile;

With potassium carbonate;

DOI:10.1016/S0957-4166(01)00530-4

Reference yield: 32.7%

trans-tert-butyl 3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate → (3S,4S)-1-tert-butoxycarbonyl-trans-3-benzylamino-4-hydroxypyrrolidine (252574-03-1)

Guidance literature:

With (S)-Mandelic acid; In water; acetonitrile; at 85 ℃; for 2h;

upstream raw materials:

tert-butyl carbazate

di-tert-butyl dicarbonate

N-(tert-butoxycarbonyl)-3-pyrroline

1-tert-butoxycarbonyl-3,4-epoxypyrrolidine

Downstream raw materials:

(3S,4S)-4-amino-1-N-tert-butyloxycarbonyl-3-hydroxypyrrolidine

(3S,4S)-tert-butyl 3-(dimethyl amino)-4-hydroxypyrrolidine-1-carboxylate

(3S,4S)-tert-butyl 3-amino-4-fluoropyrrolidine-1-carboxylate

cis-3-amino-4-fluoropyrrolidine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 -. "FUSED QUADRACYCLIC COMPOUNDS, COMPOSITIONS AND USES THEREOF". . . Retrieved 2017/08/01.
• 2、 Tsuzuki, Yasunori,Chiba, Katsumi,Mizuno, Kazuhiro,Tomita, Kyoji,Suzuki, Kenji. "Practical synthesis of (3S,4S)-3-methoxy-4-methylaminopyrrolidine". . p. 2989 - 2997. Retrieved 2007/10/03.