(3S,4S)-N-Boc-3-amino-4-hydroxypyrrolidine

Base Information

• Chemical Name: (3S,4S)-N-Boc-3-amino-4-hydroxypyrrolidine
• CAS No.: 190792-74-6
• Molecular Formula: C9H18N2O3
• Molecular Weight: 202.254
• Mol file: 190792-74-6.mol

Synonyms:1-Pyrrolidinecarboxylicacid, 3-amino-4-hydroxy-, 1,1-dimethylethyl ester, (3S-trans)-;(3S,4S)-3-Amino-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester;tert-Butyl (3S,4S)-3-Amino-4-hydroxypyrrolidine-1-carboxylate;

Chemical Property of (3S,4S)-N-Boc-3-amino-4-hydroxypyrrolidine

Chemical Property:

• Boiling Point: 308.762 °C at 760 mmHg
• PKA: 14.36±0.40(Predicted)
• Flash Point: 140.535 °C
• PSA: 75.79000
• Density: 1.179 g/cm³
• LogP: 0.56350
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

99% ^*data from raw suppliers

(3S,4S)-N-Boc-4-hydroxypyrrolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3S,4S)-N-Boc-3-amino-4-hydroxypyrrolidine

There total 14 articles about (3S,4S)-N-Boc-3-amino-4-hydroxypyrrolidine 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%

tert-butyl (+/-)-trans-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate → (3S,4S)-4-amino-1-N-tert-butyloxycarbonyl-3-hydroxypyrrolidine (190792-74-6,138026-97-8,148214-90-8,190792-75-7)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In butan-1-ol; for 10h; under 2585.81 Torr;

Reference yield: 93.0%

(3S,4S)-3-azido-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (190792-84-8) → (3S,4S)-4-amino-1-N-tert-butyloxycarbonyl-3-hydroxypyrrolidine (190792-74-6,138026-97-8,148214-90-8,190792-75-7)

Guidance literature:

With platinum(IV) oxide; hydrogen; In methanol;

DOI:10.1002/chem.201101513

Reference yield: 71.0%

(3S,4S)-3-azido-4-(trimethylsilanyloxy)pyrrolidine-1-carboxylic acid tert-butyl ester (1202067-33-1) → (3S,4S)-4-amino-1-N-tert-butyloxycarbonyl-3-hydroxypyrrolidine (190792-74-6,138026-97-8,148214-90-8,190792-75-7)

Guidance literature:

(3S,4S)-3-azido-4-(trimethylsilanyloxy)pyrrolidine-1-carboxylic acid tert-butyl ester; With trifluoroacetic acid; In methanol; for 2h;

With hydrogen; platinum(IV) oxide; In methanol; for 18h;

upstream raw materials:

(±)-tert-butyl 3-azido-4-hydroxypyrrolidine-1-carboxylate

(3S,4S)-1-tert-butoxycarbonyl-trans-3-benzylamino-4-hydroxypyrrolidine

tert-butyl carbazate

di-tert-butyl dicarbonate

Downstream raw materials:

(3S,4S)-3-benzoylamino-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester

(3S,4S)-3-amino-4-hydroxypyrrolidine dihydrochloride

(3S,4S)-tert-butyl 3-(tert-butyldiphenylsilyloxy)-4-(trifluoromethylsulfonamido)pyrrolidine-1-carboxylate

(3aS,6aR)-2-phenyl-3a,4,6,6a-tetrahydropyrrolo[3,4-d]oxazole-5-carboxylic acid tert-butyl ester

Refernces

• 1、 Martín-Rapún, Rafael,Fan, Xinyuan,Sayalero, Sonia,Bahramnejad, Mahboubeh,Cuevas, Félix,Pericàs, Miquel A.. "Highly active organocatalysts for asymmetric anti-mannich reactions". supporting information; scheme or table. p. 8780 - 8783. Retrieved 2011/09/15.
• 2、 -. "MINERALOCORTICOID RECEPTOR ANTAGONISTS AND METHODS OF USE". Page/Page column 25. . Retrieved 2009/07/10.