Benzylamine → [(1R,2S)-1-Benzyl-3-benzylamino-2-hydroxy-propyl]-carbamic acid tert-butyl ester

HRID 425002Notes

Reaction equation

HRID 425002 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].[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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][NH:27][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 11357515erythro-N-Boc-D-phenylalanine epoxide

Product 1

HCID 66703611[(1R,2S)-1-Benzyl-3-benzylamino-2-hydroxy-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 (0.263 g, 1.0 mmol) and benzylamine (0.11 mL, 1.0 mmol) gives the title compound.

Sources & evidence

ORD record
ord-dd97cc89815043d59437f0788cd33772
Source dataset
uspto-grants-2012_01
Patent number
US08106090B2

Reaction notes

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