(S)-tert-butyl 1-oxo-1-phenylbutan-2-ylcarbamate → (1R,2S)-2-amino-1-phenylbutan-1-ol

Reaction equation

Cl.N[C@@H](C)[C@@H](C1C=CC(OC)=CC=1)O.[O:15]=[C:16]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C@@H:17]([NH:20]C(=O)OC(C)(C)C)[CH2:18][CH3:19]>>[NH2:20][C@@H:17]([CH2:18][CH3:19])[C@@H:16]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[OH:15]

Participants

Reactant 2

HCID 11346070(S)-tert-butyl 1-oxo-1-phenylbutan-2-ylcarbamate

HCID 66812926(1R,2S)-2-amino-1-(4-methoxy-phenyl)propan-1-ol hydrochloride

Product 1

HCID 12562409(1R,2S)-2-amino-1-phenylbutan-1-ol

Procedure

was synthesised in the same way as 90b from (S)-tert-butyl 1-oxo-1-phenylbutan-2-ylcarbamate (95c, 209 mg, 0.795 mmol).

Sources & evidence

ORD record: ord-baeb741482af4603ba65ea7c4c0211c9
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143290B2

Reaction notes

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