Cyanogen Bromide → (4S)-4-(4,4,4-trifluoro-3-phenyl-butyl)-4,5-dihydro-oxazol-2-ylamine

HRID 885162Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:5][CH2:6][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([F:11])([F:10])[F:9])[CH2:3][OH:4].[N:18]#[C:19]Br>>[F:11][C:8]([F:9])([F:10])[CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][CH2:5][C@H:2]1[CH2:3][O:4][C:19]([NH2:18])=[N:1]1

Participants

Reactant 2

HCID 10476Cyanogen Bromide

HCID 67177841(S)-2-Amino-6,6,6-trifluoro-5-phenyl-hexan-1-ol

Product 1

HCID 45101018(4S)-4-(4,4,4-trifluoro-3-phenyl-butyl)-4,5-dihydro-oxazol-2-ylamine

Procedure

In analogy to example 1d (S)-2-amino-6,6,6-trifluoro-5-phenyl-hexan-1-ol was reacted with cyanogen bromide to give (4S)-4-(4,4,4-trifluoro-3-phenyl-butyl)-4,5-dihydro-oxazol-2-ylamine. White solid. MS (ISP): 273.1 ([M+H]+))

Sources & evidence

ORD record: ord-9e35ebdf14524154ae78634db8cf1944
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242153B2

Reaction notes

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