(2R,3S)-N-[(9-fluorenylmethoxy)carbonyl]-3-hydroxy-2-(hydroxymethyl)pyrrolidine

Base Information

Chemical Name:(2R,3S)-N-[(9-fluorenylmethoxy)carbonyl]-3-hydroxy-2-(hydroxymethyl)pyrrolidine
CAS No.:166047-90-1
Molecular Formula:C₂₀H₂₁NO₄
Molecular Weight:339.391
Hs Code.:

Synonyms:(2R,3S)-N-[(9-fluorenylmethoxy)carbonyl]-3-hydroxy-2-(hydroxymethyl)pyrrolidine

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Chemical Property of (2R,3S)-N-[(9-fluorenylmethoxy)carbonyl]-3-hydroxy-2-(hydroxymethyl)pyrrolidine

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Technology Process of (2R,3S)-N-[(9-fluorenylmethoxy)carbonyl]-3-hydroxy-2-(hydroxymethyl)pyrrolidine

There total 8 articles about (2R,3S)-N-[(9-fluorenylmethoxy)carbonyl]-3-hydroxy-2-(hydroxymethyl)pyrrolidine 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: 98.0%

: (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

: 166047-90-1
(2R,3S)-N-[(9-fluorenylmethoxy)carbonyl]-3-hydroxy-2-(hydroxymethyl)pyrrolidine

Guidance literature:: With hydrogenchloride; In ethanol;
DOI:10.1021/ja00129a039

Reference yield: 97.0%

: 296774-32-8
(2S,3S)-(3-hydroxy)pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester

: 166047-90-1
(2R,3S)-N-[(9-fluorenylmethoxy)carbonyl]-3-hydroxy-2-(hydroxymethyl)pyrrolidine

Guidance literature:: With dimethylsulfide borane complex; In tetrahydrofuran; for 2h; Heating;
DOI:10.1021/ol007029s DOI:10.1002/ejoc.200700217

Reference yield:

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 166047-90-1
(2R,3S)-N-[(9-fluorenylmethoxy)carbonyl]-3-hydroxy-2-(hydroxymethyl)pyrrolidine

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) 2,6-lutidine, TBAF, 3.) Et₃N

2: 1.) O₃, 2.) Me₂S, 3.) NaBH₄

3: 83 percent / Et₃N / CH₂Cl₂

4: 74 percent / iPr₂NEt / Heating

5: 98 percent / 1percent HCl / ethanol

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; dimethylsulfide; tetrabutyl ammonium fluoride; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane;
DOI:10.1021/ja00129a039