(2S,3S)-3-methyl-5-oxopyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Base Information

Chemical Name:(2S,3S)-3-methyl-5-oxopyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester
CAS No.:771578-95-1
Molecular Formula:C₁₈H₂₃NO₅
Molecular Weight:333.384
Hs Code.:

Synonyms:(2S,3S)-3-methyl-5-oxopyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

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Chemical Property of (2S,3S)-3-methyl-5-oxopyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

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Technology Process of (2S,3S)-3-methyl-5-oxopyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

There total 5 articles about (2S,3S)-3-methyl-5-oxopyrrolidine-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: 87.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 771578-94-0
(2S,3S)-3-methyl-5-oxopyrrolidine-2-carboxylic acid benzyl ester

: 771578-95-1
(2S,3S)-3-methyl-5-oxopyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Guidance literature:: With dmap; In acetonitrile; at 20 ℃; for 9.5h;
DOI:10.1016/j.tet.2004.06.111

Reference yield:

: 103201-79-2,1820583-17-2
(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

: 771578-95-1
(2S,3S)-3-methyl-5-oxopyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 71 percent / diisopropylamine; n-BuLi; N-tert-butyl benzenesulfinimidoyl chloride / tetrahydrofuran; hexane / -78 - -10 °C

2: 86 percent / CuI; Me₃SiCl / tetrahydrofuran; diethyl ether / 1 h / -78 °C

3: 65 percent / NaIO₄ / RuCl₃ / CCl₄; acetonitrile; H₂O / 24 h / 20 °C

4: 65 percent / TsOH*H₂O / toluene / 14.5 h / Heating

5: 87 percent / DMAP / acetonitrile / 9.5 h / 20 °C

With dmap; sodium periodate; copper(l) iodide; n-butyllithium; chloro-trimethyl-silane; N-tert-butyl benzenesulfinimidoyl chloride; toluene-4-sulfonic acid; diisopropylamine; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; diethyl ether; hexane; water; toluene; acetonitrile; 2: Michael reaction;
DOI:10.1016/j.tet.2004.06.111

Reference yield:

: 134107-65-6
(3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one

: 771578-95-1
(2S,3S)-3-methyl-5-oxopyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 86 percent / CuI; Me₃SiCl / tetrahydrofuran; diethyl ether / 1 h / -78 °C

2: 65 percent / NaIO₄ / RuCl₃ / CCl₄; acetonitrile; H₂O / 24 h / 20 °C

3: 65 percent / TsOH*H₂O / toluene / 14.5 h / Heating

4: 87 percent / DMAP / acetonitrile / 9.5 h / 20 °C

With dmap; sodium periodate; copper(l) iodide; chloro-trimethyl-silane; toluene-4-sulfonic acid; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; diethyl ether; water; toluene; acetonitrile; 1: Michael reaction;
DOI:10.1016/j.tet.2004.06.111