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

Base Information

Chemical Name:(2R,3S,4S)-1-tert-butoxycarbonyl-3-benzoyloxy-2-hydroxymethyl-4-methylpyrrolidine
CAS No.:208709-15-3
Molecular Formula:C₁₈H₂₅NO₅
Molecular Weight:335.4
Hs Code.:

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

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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,4S)-1-tert-butoxycarbonyl-3-benzoyloxy-2-hydroxymethyl-4-methylpyrrolidine

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

There total 8 articles about (2R,3S,4S)-1-tert-butoxycarbonyl-3-benzoyloxy-2-hydroxymethyl-4-methylpyrrolidine 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: 79.0%

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

: 208709-15-3
(2R,3S,4S)-1-tert-butoxycarbonyl-3-benzoyloxy-2-hydroxymethyl-4-methylpyrrolidine

Guidance literature:: With hydrogen; platinum(IV) oxide; In ethyl acetate; for 1.5h;
DOI:10.1016/S0040-4020(00)00117-4

Reference yield: 32.0%

: 98-88-4
benzoyl chloride

: 208711-86-8
(2R,3S)-2-(1-Ethoxy-ethoxymethyl)-3,5-dihydroxy-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

: 208709-15-3
(2R,3S,4S)-1-tert-butoxycarbonyl-3-benzoyloxy-2-hydroxymethyl-4-methylpyrrolidine

: 208709-16-4
(2R,3S,4R)-1-tert-butoxycarbonyl-3-benzoyloxy-2-hydroxymethyl-4-methylpyrrolidine

Guidance literature:: benzoyl chloride; (2R,3S)-2-(1-Ethoxy-ethoxymethyl)-3,5-dihydroxy-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester; With triethylamine; In dichloromethane; at 40 ℃; for 24h;

With sodium cyanoborohydride; acetic acid; at 30 ℃; for 1.5h;
DOI:10.1016/S0040-4020(00)00117-4

Reference yield:

: 98-88-4
benzoyl chloride

: 208709-15-3
(2R,3S,4S)-1-tert-butoxycarbonyl-3-benzoyloxy-2-hydroxymethyl-4-methylpyrrolidine

Guidance literature:: Multi-step reaction with 5 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

5: 79 percent / H₂ / PtO₂ / ethyl acetate / 1.5 h

With sodium hydroxide; hydrogen; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; platinum(IV) oxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; 1: Esterification / 2: Oxidation / 3: Cope elimination / 4: Hydrolysis / 5: Catalytic hydrogenation;
DOI:10.1016/S0040-4020(00)00117-4