(2R,3S,4S)-2-acetoxymethyl-4-(N,N-dimethyl)aminomethyl-3-benzoyloxy-1-tert-butoxycarbonylpyrrolidine

Base Information

Chemical Name:(2R,3S,4S)-2-acetoxymethyl-4-(N,N-dimethyl)aminomethyl-3-benzoyloxy-1-tert-butoxycarbonylpyrrolidine
CAS No.:276697-19-9
Molecular Formula:C₂₂H₃₂N₂O₆
Molecular Weight:420.506
Hs Code.:

Synonyms:(2R,3S,4S)-2-acetoxymethyl-4-(N,N-dimethyl)aminomethyl-3-benzoyloxy-1-tert-butoxycarbonylpyrrolidine

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Chemical Property of (2R,3S,4S)-2-acetoxymethyl-4-(N,N-dimethyl)aminomethyl-3-benzoyloxy-1-tert-butoxycarbonylpyrrolidine

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Technology Process of (2R,3S,4S)-2-acetoxymethyl-4-(N,N-dimethyl)aminomethyl-3-benzoyloxy-1-tert-butoxycarbonylpyrrolidine

There total 1 articles about (2R,3S,4S)-2-acetoxymethyl-4-(N,N-dimethyl)aminomethyl-3-benzoyloxy-1-tert-butoxycarbonylpyrrolidine 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: 93.0%

: 98-88-4
benzoyl chloride

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

: 276697-19-9
(2R,3S,4S)-2-acetoxymethyl-4-(N,N-dimethyl)aminomethyl-3-benzoyloxy-1-tert-butoxycarbonylpyrrolidine

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 27h;
DOI:10.1016/S0040-4020(00)00117-4

Reference yield: 98.0%

: 276697-19-9
(2R,3S,4S)-2-acetoxymethyl-4-(N,N-dimethyl)aminomethyl-3-benzoyloxy-1-tert-butoxycarbonylpyrrolidine

: 276697-21-3
(2R,3S,4S)-2-acetoxymethyl-4-(N,N-dimethyl,N-oxy)aminomethyl-3-benzoyloxy-1-tert-butoxycarbonylpyrrolidine

Guidance literature:: With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 0.0833333h;
DOI:10.1016/S0040-4020(00)00117-4

Reference yield:

: 276697-19-9
(2R,3S,4S)-2-acetoxymethyl-4-(N,N-dimethyl)aminomethyl-3-benzoyloxy-1-tert-butoxycarbonylpyrrolidine

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

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 0.08 h

2: 87 percent / tetrahydrofuran; toluene / 5 h / 85 °C

3: 72 percent / 0.05 N NaOH / methanol / 0.4 h / 20 °C

4: 79 percent / H₂ / PtO₂ / ethyl acetate / 1.5 h

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