(2S,3R)-3-(4-Cyano-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Base Information

Chemical Name:(2S,3R)-3-(4-Cyano-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester
CAS No.:540508-35-8
Molecular Formula:C₁₇H₂₀N₂O₅
Molecular Weight:332.356
Hs Code.:

Synonyms:(2S,3R)-3-(4-Cyano-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

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Chemical Property of (2S,3R)-3-(4-Cyano-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

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Technology Process of (2S,3R)-3-(4-Cyano-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

There total 4 articles about (2S,3R)-3-(4-Cyano-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 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: 81.0%

: 540508-62-1
(2R,3R)-3-(4-Cyano-phenoxy)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

: 540508-35-8
(2S,3R)-3-(4-Cyano-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Guidance literature:: (2R,3R)-3-(4-Cyano-phenoxy)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester; With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In dichloromethane; at -78 ℃; for 3h; Swern-Masamune oxidation;

With potassium permanganate; In phosphate buffer; tert-butyl alcohol; at 20 ℃; for 1h; pH=4.12;
DOI:10.1016/S0040-4039(03)00278-8

Reference yield:

: 123278-55-7
(4R,5S)-5-<(1,1-dimethylethyl)dimethylsilyl>oxymethyl-4-hydroxy-1-<(1,1-dimethylethoxy)carbonyl>-pyrrolidin-2-one

: 540508-35-8
(2S,3R)-3-(4-Cyano-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 88 percent / BH₃*SMe₂ / tetrahydrofuran / 5 h / Heating

2.1: 78 percent / NaH / dimethylformamide / 4 h / -30 °C

3.1: 88 percent / AcOH / tetrahydrofuran; H₂O / 15 h / 40 - 45 °C

4.1: NEt₃; TFAA; DMSO / CH₂Cl₂ / 3 h / -78 °C / Swern-Masamune oxidation

4.2: 81 percent / KMnO₄ / aq. phosphate buffer; 2-methyl-propan-2-ol / 1 h / 20 °C / pH 4.12

With dimethylsulfide borane complex; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(03)00278-8

Reference yield:

: 128836-20-4
tert-butyl (2R,3R)-2-[(tert-butyldimethylsiloxy)methyl]-3-hydroxypyrrolidine-1-carboxylate

: 540508-35-8
(2S,3R)-3-(4-Cyano-phenoxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 78 percent / NaH / dimethylformamide / 4 h / -30 °C

2.1: 88 percent / AcOH / tetrahydrofuran; H₂O / 15 h / 40 - 45 °C

3.1: NEt₃; TFAA; DMSO / CH₂Cl₂ / 3 h / -78 °C / Swern-Masamune oxidation

3.2: 81 percent / KMnO₄ / aq. phosphate buffer; 2-methyl-propan-2-ol / 1 h / 20 °C / pH 4.12

With sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(03)00278-8