(2S,3R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-oxopyrrolidine-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,3R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-oxopyrrolidine-2-carboxylic acid methyl ester
CAS No.:169774-61-2
Molecular Formula:C₁₉H₂₃NO₆
Molecular Weight:361.395
Hs Code.:

Synonyms:(2S,3R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-oxopyrrolidine-2-carboxylic acid methyl ester

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Chemical Property of (2S,3R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-oxopyrrolidine-2-carboxylic acid methyl ester

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Technology Process of (2S,3R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-oxopyrrolidine-2-carboxylic acid methyl ester

There total 5 articles about (2S,3R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-oxopyrrolidine-2-carboxylic acid 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: 30.0%

: 5292-43-3
bromoacetic acid tert-butyl ester

: 169774-59-8
methyl (2S)-1-benzoyl-4-oxo-2-pyrrolidinecarboxylate

: 169774-61-2
(2S,3R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-oxopyrrolidine-2-carboxylic acid methyl ester

Guidance literature:: methyl (2S)-1-benzoyl-4-oxo-2-pyrrolidinecarboxylate; With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

bromoacetic acid tert-butyl ester; With sodium iodide; In tetrahydrofuran; hexane; at -60 - -42 ℃; for 1h; Inert atmosphere;
DOI:10.1039/c4ob02002b

Reference yield:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 169774-61-2
(2S,3R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-oxopyrrolidine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 94 percent / NaHCO₃ / H₂O; tetrahydrofuran / 1.5 h / Ambient temperature

2: 85 percent / RuCl₃*3H₂O, NaIO₄ / acetonitrile; CCl₄; H₂O / 3.5 h / Ambient temperature

3: 100 percent / benzene / 0.33 h / Heating

4: 1.) K₂CO₃, 2.) acetic acid / 1.) acetonitrile, reflux, 18 h, 2.) CHCl₃, H₂O, room temperature, 5.5 h.

With ruthenium trichloride; sodium periodate; sodium hydrogencarbonate; potassium carbonate; acetic acid; In tetrahydrofuran; tetrachloromethane; water; acetonitrile; benzene;
DOI:10.1016/S0040-4020(97)00190-7

Reference yield:

: 31560-20-0,120806-96-4
(2S,4R)-1-benzoyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester

: 169774-61-2
(2S,3R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-oxopyrrolidine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 85 percent / RuCl₃*3H₂O, NaIO₄ / acetonitrile; CCl₄; H₂O / 3.5 h / Ambient temperature

2: 100 percent / benzene / 0.33 h / Heating

3: 1.) K₂CO₃, 2.) acetic acid / 1.) acetonitrile, reflux, 18 h, 2.) CHCl₃, H₂O, room temperature, 5.5 h.

With ruthenium trichloride; sodium periodate; potassium carbonate; acetic acid; In tetrachloromethane; water; acetonitrile; benzene;
DOI:10.1016/S0040-4020(97)00190-7