(S)-(+)-2-(Methoxymethyl)pyrrolidine → [(1R,2S)-1-Benzyl-2-hydroxy-3-([2S]-2-methoxymethyl-pyrrolidin-1-yl)-propyl]-carbamic acid tert-butyl ester

HRID 424997Notes

Reaction equation

HRID 424997 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C@@H:8]([C@@H:16]1[CH2:18][O:17]1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:20][O:21][CH2:22][C@@H:23]1[CH2:27][CH2:26][CH2:25][NH:24]1>>[C:1]([O:5][C:6](=[O:19])[NH:7][C@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C@@H:16]([OH:17])[CH2:18][N:24]1[CH2:25][CH2:26][CH2:27][C@H:23]1[CH2:22][O:21][CH3:20])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 671217(S)-(+)-2-(Methoxymethyl)pyrrolidineHCID 11357515erythro-N-Boc-D-phenylalanine epoxide

Product 1

HCID 66703734[(1R,2S)-1-Benzyl-2-hydroxy-3-([2S]-2-methoxymethyl-pyrrolidin-1-yl)-propyl]-carbamic acid tert-butyl ester

Procedure

Using general procedure 1 and purification method D with [(1R)-1-{(2R)-oxiran-2-yl}-2-phenyl-ethyl]carbamic acid tert-butylester (0.10 g, 0.38 mmol) and (2S)-2-methoxymethyl-pyrrolidine (0.087 g, 0.76 mmol) gives the title compound.

Sources & evidence

ORD record
ord-087be42f93784f70ab9a7046cde33b95
Source dataset
uspto-grants-2012_01
Patent number
US08106090B2

Reaction notes

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