Cyanogen Bromide → (S)-4-{2-[1-(4-chloro-phenyl)-cyclopropyl]-ethyl}-4,5-dihydro-oxazol-2-ylamine

HRID 885181Notes

Reaction equation

HRID 885181 reaction equation
[NH2:1][C@@H:2]([CH2:5][CH2:6][C:7]1([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:9][CH2:8]1)[CH2:3][OH:4].[N:17]#[C:18]Br>>[Cl:16][C:13]1[CH:12]=[CH:11][C:10]([C:7]2([CH2:6][CH2:5][C@H:2]3[CH2:3][O:4][C:18]([NH2:17])=[N:1]3)[CH2:9][CH2:8]2)=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 10476Cyanogen BromideHCID 67179178(S)-2-amino-4-[1-(4-chloro-phenyl)-cyclopropyl]-butan-1-ol

Product 1

HCID 45101109(S)-4-{2-[1-(4-chloro-phenyl)-cyclopropyl]-ethyl}-4,5-dihydro-oxazol-2-ylamine

Procedure

In analogy to example 1d (S)-2-amino-4-[1-(4-chloro-phenyl)-cyclopropyl]-butan-1-ol was reacted with cyanogen bromide to give (S)-4-{2-[1-(4-chloro-phenyl)-cyclopropyl]-ethyl}-4,5-dihydro-oxazol-2-ylamine. White solid. MS (ISP): 265.1 ([M+H]+))

Sources & evidence

ORD record
ord-6666c05445e642529eea207343e39c67
Source dataset
uspto-grants-2012_08
Patent number
US08242153B2

Reaction notes

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