(2R,3S,4S)-4-Isopropenyl-3-(2-oxo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Base Information

Chemical Name:(2R,3S,4S)-4-Isopropenyl-3-(2-oxo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
CAS No.:391677-19-3
Molecular Formula:C₁₉H₂₃NO₅
Molecular Weight:345.395
Hs Code.:

Synonyms:(2R,3S,4S)-4-Isopropenyl-3-(2-oxo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

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Chemical Property of (2R,3S,4S)-4-Isopropenyl-3-(2-oxo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

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Technology Process of (2R,3S,4S)-4-Isopropenyl-3-(2-oxo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

There total 17 articles about (2R,3S,4S)-4-Isopropenyl-3-(2-oxo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl 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: 79.0%

: (2R,3S,4S)-3-((S)-2-Hydroxy-2-oxiranyl-ethyl)-4-isopropenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

: 391677-19-3
(2R,3S,4S)-4-Isopropenyl-3-(2-oxo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Guidance literature:: (2R,3S,4S)-3-((S)-2-Hydroxy-2-oxiranyl-ethyl)-4-isopropenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester; With sodium hydride; thiophenol; In tetrahydrofuran;

With sodium periodate; at 0 ℃;
DOI:10.1016/S0040-4039(01)01558-1

Reference yield:

: (1R,3R,5R,6R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-ol

: 391677-19-3
(2R,3S,4S)-4-Isopropenyl-3-(2-oxo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: Et₃N / CH₂Cl₂

2.1: sodium azide / dimethylformamide / 80 °C

2.2: imidazole

3.1: LiAlH₄ / diethyl ether / 0 °C

4.1: K₂CO₃ / 0 °C

5.1: 83 percent / NaH / dimethylformamide / 0 °C

6.1: 98 percent / sodium hydrogen carbonate / diphenyl ether / 0.5 h / Heating

7.1: 97 percent / TBAF / tetrahydrofuran

8.1: Et₃N / CH₂Cl₂

9.1: LiI / tetrahydrofuran / Heating

10.1: 90 percent / zinc / methanol; acetic acid / Heating

11.1: 83 percent / TPAP-NMO / CH₂Cl₂; acetonitrile

12.1: 75 percent / NaOMe / 20 °C

13.1: 78 percent / tert-butyl hydroperoxide; VO(acac)2 / benzene / 40 °C

14.1: thiophenol; NaH / tetrahydrofuran

14.2: 79 percent / aq. NaIO₄ / 0 °C

With tert.-butylhydroperoxide; lithium aluminium tetrahydride; sodium azide; tetrapropylammonium perruthennate; bis(acetylacetonate)oxovanadium; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; thiophenol; 4-methylmorpholine N-oxide; triethylamine; lithium iodide; zinc; In tetrahydrofuran; methanol; diphenylether; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1016/S0040-4039(01)01558-1

Reference yield:

: (1R,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-one

: 391677-19-3
(2R,3S,4S)-4-Isopropenyl-3-(2-oxo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 15 steps

1.1: 98 percent / NaBH₄; CeCl₃*7H₂O / methanol / -78 °C

2.1: Et₃N / CH₂Cl₂

3.1: sodium azide / dimethylformamide / 80 °C

3.2: imidazole

4.1: LiAlH₄ / diethyl ether / 0 °C

5.1: K₂CO₃ / 0 °C

6.1: 83 percent / NaH / dimethylformamide / 0 °C

7.1: 98 percent / sodium hydrogen carbonate / diphenyl ether / 0.5 h / Heating

8.1: 97 percent / TBAF / tetrahydrofuran

9.1: Et₃N / CH₂Cl₂

10.1: LiI / tetrahydrofuran / Heating

11.1: 90 percent / zinc / methanol; acetic acid / Heating

12.1: 83 percent / TPAP-NMO / CH₂Cl₂; acetonitrile

13.1: 75 percent / NaOMe / 20 °C

14.1: 78 percent / tert-butyl hydroperoxide; VO(acac)2 / benzene / 40 °C

15.1: thiophenol; NaH / tetrahydrofuran

15.2: 79 percent / aq. NaIO₄ / 0 °C

With tert.-butylhydroperoxide; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; cerium(III) chloride; tetrapropylammonium perruthennate; bis(acetylacetonate)oxovanadium; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; thiophenol; 4-methylmorpholine N-oxide; triethylamine; lithium iodide; zinc; In tetrahydrofuran; methanol; diphenylether; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1016/S0040-4039(01)01558-1