Isobutyraldehyde → ((R)-2-(2-methylpropyl)amino-1-phenyl-ethyl)-carbamic acid tert-butyl ester

HRID 1711178Notes

Reaction equation

[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][NH2:10])([CH3:4])([CH3:3])[CH3:2].[CH3:18][CH:19]([CH3:22])[CH:20]=O>>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:9][NH:10][CH2:18][CH:19]([CH3:22])[CH3:20])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 6561Isobutyraldehyde

HCID 15675183[(1R)-2-AMINO-1-PHENYLETHYL]-CARBAMIC ACID 1,1-DIMETHYLETHYL ESTER

Product 1

HCID 68777146((R)-2-(2-methylpropyl)amino-1-phenyl-ethyl)-carbamic acid tert-butyl esterYield 91.1%

Procedure

Using general procedure A, ((R)-2-amino-1-phenyl-ethyl)-carbamic acid tert-butyl ester (472 mg, 2.00 mmol) and 2-methylpropionaldehyde (181 μL, 2.00 mmol) afforded ((R)-2-(2-methylpropyl)amino-1-phenyl-ethyl)-carbamic acid tert-butyl ester (533 mg, 91%).

Sources & evidence

ORD record: ord-703293cd9d094e5294a9f3696b7e9443
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790747B2

Reaction notes

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