4S-isopropyl-5S-phenylpyrrolidine-1,2S-dicarboxylic acid 1-tert-butyl ester 2S-methyl ester

Base Information

Chemical Name:4S-isopropyl-5S-phenylpyrrolidine-1,2S-dicarboxylic acid 1-tert-butyl ester 2S-methyl ester
CAS No.:441794-53-2
Molecular Formula:C₂₀H₂₉NO₄
Molecular Weight:347.455
Hs Code.:

Synonyms:4S-isopropyl-5S-phenylpyrrolidine-1,2S-dicarboxylic acid 1-tert-butyl ester 2S-methyl ester

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Chemical Property of 4S-isopropyl-5S-phenylpyrrolidine-1,2S-dicarboxylic acid 1-tert-butyl ester 2S-methyl ester

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Technology Process of 4S-isopropyl-5S-phenylpyrrolidine-1,2S-dicarboxylic acid 1-tert-butyl ester 2S-methyl ester

There total 7 articles about 4S-isopropyl-5S-phenylpyrrolidine-1,2S-dicarboxylic acid 1-tert-butyl ester 2S-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: 89.0%

: phenylmagnesium bromide

: 441794-52-1
(2S,4S)-4-Isopropyl-5-methoxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

: 441794-53-2
4S-isopropyl-5S-phenylpyrrolidine-1,2S-dicarboxylic acid 1-tert-butyl ester 2S-methyl ester

Guidance literature:: With copper bromide dimethyl sulfide complex; boron trifluoride diethyl etherate; In diethyl ether; at -78 - 20 ℃;
DOI:10.1021/jo011184i

Reference yield:

: 108963-96-8
(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one

: 441794-53-2
4S-isopropyl-5S-phenylpyrrolidine-1,2S-dicarboxylic acid 1-tert-butyl ester 2S-methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / LiHMDS / tetrahydrofuran / 4 h / -78 °C

2: 70 percent / imidazole / CH₂Cl₂ / 2 h / 0 °C

3: DIBAl-H / tetrahydrofuran / 2 h / -78 °C

4: 11.4 g / pTSA

5: 72 percent / MsCl; Et₃N; DMAP / CH₂Cl₂

6: 82 percent / H₂; NaHCO₃ / Pd/C / ethyl acetate

7: 89 percent / CuBr₂*Me₂S; BF₃*Et₂O / diethyl ether / -78 - 20 °C

With 1H-imidazole; dmap; copper bromide dimethyl sulfide complex; boron trifluoride diethyl etherate; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate;
DOI:10.1021/jo011184i

Reference yield:

: 4-(1-hydroxy-1-methylethyl)-5-methoxypyrrolidine-1,2S-dicarboxylic acid 1-tert-butyl ester 2S-methyl ester

: 441794-53-2
4S-isopropyl-5S-phenylpyrrolidine-1,2S-dicarboxylic acid 1-tert-butyl ester 2S-methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 72 percent / MsCl; Et₃N; DMAP / CH₂Cl₂

2: 82 percent / H₂; NaHCO₃ / Pd/C / ethyl acetate

3: 89 percent / CuBr₂*Me₂S; BF₃*Et₂O / diethyl ether / -78 - 20 °C

With dmap; copper bromide dimethyl sulfide complex; boron trifluoride diethyl etherate; hydrogen; sodium hydrogencarbonate; methanesulfonyl chloride; triethylamine; palladium on activated charcoal; In diethyl ether; dichloromethane; ethyl acetate;
DOI:10.1021/jo011184i