(2R,4S)-4-Hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

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Chemical Name:(2R,4S)-4-Hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester
CAS No.:857478-47-8
Molecular Formula:C₁₈H₂₅NO₅
Molecular Weight:335.4
Hs Code.:

Synonyms:(2R,4S)-4-Hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

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Chemical Property of (2R,4S)-4-Hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

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Technology Process of (2R,4S)-4-Hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

There total 4 articles about (2R,4S)-4-Hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester 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: 91.0%

: 857478-26-3
(2R,4S)-1-(tert-butoxycarbonyl)-2-benzyloxycarbonyl-4-(tert-butyldimethylsiloxy)methylpyrrolidine

: 857478-47-8
(2R,4S)-4-Hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3h;
DOI:10.1021/ol050991r

Reference yield:

: 4-hydroxymethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

: 857478-47-8
(2R,4S)-4-Hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 53 percent / imidazole / dimethylformamide / 6 h / 20 °C

2.1: DIBAL-H / tetrahydrofuran; toluene / 1 h / -78 °C

2.2: 95 percent / Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -78 °C

3.1: 91 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol050991r

Reference yield:

: 857478-22-9
(3R,5R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)methyl-5-benzyloxycarbonyl-pyrrolidin-2-one

: 857478-47-8
(2R,4S)-4-Hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: DIBAL-H / tetrahydrofuran; toluene / 1 h / -78 °C

1.2: 95 percent / Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -78 °C

2.1: 91 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

With tetrabutyl ammonium fluoride; diisobutylaluminium hydride; In tetrahydrofuran; toluene;
DOI:10.1021/ol050991r