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

HRID 424999Notes

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][NH2:21]>>[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:21][CH3:20])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 6329Methylamine

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

Product 1

HCID 66703655[(1R,2S)-1-Benzyl-2-hydroxy-3-methylamino-propyl]-carbamic acid tert-butyl ester

Procedure

Using general procedure 1 with [(1R)-1-{(2R)-oxiran-2-yl}-2-phenyl-ethyl]carbamic acid tert-butylester (0.50 g, 1.9 mmol) and methylamine (10 mL, 8 M solution in ethanol, mmol; used as solvent) gives the title compound.

Sources & evidence

ORD record: ord-9d07d4661392404e8e5f959cfa4f623e
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106090B2

Reaction notes

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