(2R,3S)-3-benzoyloxy-1-tert-butoxycarbonyl-2-hydroxymethyl-4-exo-methylenepyrrolidine

Base Information

Chemical Name:(2R,3S)-3-benzoyloxy-1-tert-butoxycarbonyl-2-hydroxymethyl-4-exo-methylenepyrrolidine
CAS No.:276697-25-7
Molecular Formula:C₁₈H₂₃NO₅
Molecular Weight:333.384
Hs Code.:

Synonyms:(2R,3S)-3-benzoyloxy-1-tert-butoxycarbonyl-2-hydroxymethyl-4-exo-methylenepyrrolidine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3S)-3-benzoyloxy-1-tert-butoxycarbonyl-2-hydroxymethyl-4-exo-methylenepyrrolidine

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Technology Process of (2R,3S)-3-benzoyloxy-1-tert-butoxycarbonyl-2-hydroxymethyl-4-exo-methylenepyrrolidine

There total 5 articles about (2R,3S)-3-benzoyloxy-1-tert-butoxycarbonyl-2-hydroxymethyl-4-exo-methylenepyrrolidine 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: 72.0%

: 276697-23-5
(2R,3S)-2-acetoxymethyl-3-benzoyloxy-1-tert-butoxycarbonyl-4-exo-methylenepyrrolidine

: (2R,3S)-3-Hydroxy-2-hydroxymethyl-4-methylene-pyrrolidine-1-carboxylic acid tert-butyl ester

: 276697-25-7
(2R,3S)-3-benzoyloxy-1-tert-butoxycarbonyl-2-hydroxymethyl-4-exo-methylenepyrrolidine

Guidance literature:: With sodium hydroxide; In methanol; at 20 ℃; for 0.4h;
DOI:10.1016/S0040-4020(00)00117-4

Reference yield:

: 98-88-4
benzoyl chloride

: 276697-25-7
(2R,3S)-3-benzoyloxy-1-tert-butoxycarbonyl-2-hydroxymethyl-4-exo-methylenepyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / Et₃N / CH₂Cl₂ / 27 h / 20 °C

2: 98 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 0.08 h

3: 87 percent / tetrahydrofuran; toluene / 5 h / 85 °C

4: 72 percent / 0.05 N NaOH / methanol / 0.4 h / 20 °C

With sodium hydroxide; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: Esterification / 2: Oxidation / 3: Cope elimination / 4: Hydrolysis;
DOI:10.1016/S0040-4020(00)00117-4

Reference yield:

: (2R,3S,4S)-2-acetoxymethyl-4-(N,N-dimethyl)aminomethyl-1-tert-butoxycarbonyl-3-hydroxypyrrolidine

: 276697-25-7
(2R,3S)-3-benzoyloxy-1-tert-butoxycarbonyl-2-hydroxymethyl-4-exo-methylenepyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / Et₃N / CH₂Cl₂ / 27 h / 20 °C

2: 98 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 0.08 h

3: 87 percent / tetrahydrofuran; toluene / 5 h / 85 °C

4: 72 percent / 0.05 N NaOH / methanol / 0.4 h / 20 °C

With sodium hydroxide; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: Esterification / 2: Oxidation / 3: Cope elimination / 4: Hydrolysis;
DOI:10.1016/S0040-4020(00)00117-4