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

Base Information

Chemical Name:(3R,5R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)methyl-5-benzyloxycarbonyl-pyrrolidin-2-one
CAS No.:857478-22-9
Molecular Formula:C₂₄H₃₇NO₆Si
Molecular Weight:463.646
Hs Code.:

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

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Chemical Property of (3R,5R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)methyl-5-benzyloxycarbonyl-pyrrolidin-2-one

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Technology Process of (3R,5R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)methyl-5-benzyloxycarbonyl-pyrrolidin-2-one

There total 2 articles about (3R,5R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)methyl-5-benzyloxycarbonyl-pyrrolidin-2-one 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: 53.0%

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

: 18162-48-6
tert-butyldimethylsilyl chloride

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

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

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 6h;
DOI:10.1021/ol050991r

Reference yield:

: 400626-71-3
2-benzyl 1-(tert-butyl) (R)-5-oxopyrrolidine-1,2-dicarboxylate

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

Guidance literature:: Multi-step reaction with 2 steps

1.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / 3 h / -78 °C

1.2: 58 percent / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 53 percent / imidazole / dimethylformamide / 6 h / 20 °C

With 1H-imidazole; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol050991r

Reference yield: 95.0%

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

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

Guidance literature:: (3R,5R)-1-(tert-butoxycarbonyl)-3-(tert-butyldimethylsiloxy)methyl-5-benzyloxycarbonyl-pyrrolidin-2-one; With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 ℃; for 1h;

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1.5h;
DOI:10.1021/ol050991r