(2S,4S)-tert-butyl 4-(tert-butyldiphenylsilyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (2S,4S)-tert-butyl 4-(tert-butyldiphenylsilyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate
• CAS No.: 887923-73-1
• Molecular Formula: C₂₆H₃₇NO₄Si
• Molecular Weight: 455.67
• Mol file: 887923-73-1.mol

Synonyms:(2S,4S)-tert-butyl 4-(tert-butyldiphenylsilyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Chemical Property of (2S,4S)-tert-butyl 4-(tert-butyldiphenylsilyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-tert-butyl 4-(tert-butyldiphenylsilyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

There total 9 articles about (2S,4S)-tert-butyl 4-(tert-butyldiphenylsilyloxy)-2-(hydroxymethyl)pyrrolidine-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: 70.0%

ethyl (2S,4S)-N-tert-butyloxycarbonyl-4-tert-butyldiphenylsiloxyprolinate (502442-64-0) → (2S,4S)-tert-butyl 4-(tert-butyldiphenylsilyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (887923-73-1)

Guidance literature:

With sodium tetrahydroborate; ethanol;

DOI:10.1246/cl.2006.300

Reference yield:

(2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (1157902-48-1) → (2S,4S)-tert-butyl 4-(tert-butyldiphenylsilyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (887923-73-1)

Guidance literature:

(2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester; With sodium tetrahydroborate; In tetrahydrofuran; at 70 ℃; for 4h;

With water; sodium hydrogencarbonate; In tetrahydrofuran; at 20 ℃;

Reference yield:

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester (74844-91-0,114676-69-6,135042-17-0,227935-38-8,102195-79-9) → (2S,4S)-tert-butyl 4-(tert-butyldiphenylsilyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (887923-73-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-imidazole / dichloromethane / 18 h / 20 °C

2: sodium tetrahydroborate / tetrahydrofuran / 4 h / 70 °C

With 1H-imidazole; sodium tetrahydroborate; In tetrahydrofuran; dichloromethane;

upstream raw materials:

ethyl (2S,4S)-N-tert-butyloxycarbonyl-4-tert-butyldiphenylsiloxyprolinate

di-tert-butyl dicarbonate

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

(2S,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester

Downstream raw materials:

(2S,4S)-tert-butyl 4-(tert-butyldiphenylsilanyloxy)-2-((2-methoxyethoxy)methyl)pyrrolidine-1-carboxylate

(2S,4S)-tert-butyl 4-hydroxy-2-((2-methoxyethoxy)methyl)pyrrolidine-1-carboxylate

(2S,4S)-tert-butyl 2-((2-methoxyethoxy)methyl)-4-(tosyloxy)pyrrolidine-1-carboxylate

4-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-[(tert-butoxycarbonylmethyl-methyl-amino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester