(2S,4S)-4-(2-Hydroxy-2-phenyl-ethyl)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Base Information

Chemical Name:(2S,4S)-4-(2-Hydroxy-2-phenyl-ethyl)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester
CAS No.:314082-73-0
Molecular Formula:C₂₅H₃₁NO₅
Molecular Weight:425.525
Hs Code.:

Synonyms:(2S,4S)-4-(2-Hydroxy-2-phenyl-ethyl)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

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Chemical Property of (2S,4S)-4-(2-Hydroxy-2-phenyl-ethyl)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

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Technology Process of (2S,4S)-4-(2-Hydroxy-2-phenyl-ethyl)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

There total 6 articles about (2S,4S)-4-(2-Hydroxy-2-phenyl-ethyl)-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: 57.0%

: phenylmagnesium bromide

: 204914-89-6
(2S,4S)-4-(2-Oxo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

: 314082-73-0
(2S,4S)-4-(2-Hydroxy-2-phenyl-ethyl)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Guidance literature:: In tetrahydrofuran; diethyl ether; at -78 ℃;
DOI:10.1016/S0960-894X(00)00465-0

Reference yield:

: 113400-36-5,400626-71-3
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 314082-73-0
(2S,4S)-4-(2-Hydroxy-2-phenyl-ethyl)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: LiHMDS / tetrahydrofuran / -78 °C

1.2: tetrahydrofuran / -78 °C

2.1: LiEt₃BH / tetrahydrofuran / -78 °C

3.1: HSiEt₃; BF₃*Et₂O / CH₂Cl₂ / -78 °C

4.1: 100 percent / OsO₄; NMMO / 2-methyl-propan-2-ol; H₂O / 20 °C

5.1: 100 percent / aq. NaIO₄ / tetrahydrofuran / 0 - 20 °C

6.1: 57 percent / diethyl ether; tetrahydrofuran / -78 °C

With triethylsilane; sodium periodate; osmium(VIII) oxide; boron trifluoride diethyl etherate; lithium triethylborohydride; 4-methylmorpholine N-oxide; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; water; tert-butyl alcohol; 1.1: Metallation / 1.2: Alkylation / 2.1: Reduction / 3.1: Reduction / 4.1: dihydroxylation / 5.1: oxidative cleavage / 6.1: Grignard reaction;
DOI:10.1016/S0960-894X(00)00465-0

Reference yield:

: 314082-71-8
benzyl (2S,4R)-4-allyl-1N-tert-butoxycarbonylpyrrolidine-2-carboxylate

: 314082-73-0
(2S,4S)-4-(2-Hydroxy-2-phenyl-ethyl)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / OsO₄; NMMO / 2-methyl-propan-2-ol; H₂O / 20 °C

2: 100 percent / aq. NaIO₄ / tetrahydrofuran / 0 - 20 °C

3: 57 percent / diethyl ether; tetrahydrofuran / -78 °C

With sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; water; tert-butyl alcohol; 1: dihydroxylation / 2: oxidative cleavage / 3: Grignard reaction;
DOI:10.1016/S0960-894X(00)00465-0