Cyanogen Bromide → (S)-4-(2-phenyl-propyl)-4,5-dihydro-oxazol-2-ylamine

Reaction equation

[NH2:1][C@@H:2]([CH2:5][CH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:7])[CH2:3][OH:4].[N:14]#[C:15]Br>>[C:8]1([CH:6]([CH3:7])[CH2:5][C@H:2]2[CH2:3][O:4][C:15]([NH2:14])=[N:1]2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Reactant 2

HCID 10476Cyanogen Bromide

HCID 68709718(S)-2-amino-4-phenyl-pentan-1-ol

Product 1

HCID 59323620(S)-4-(2-phenyl-propyl)-4,5-dihydro-oxazol-2-ylamine

Procedure

In analogy to example 1b (S)-2-amino-4-phenyl-pentan-1-ol was reacted with cyanogen bromide to give (S)-4-(2-phenyl-propyl)-4,5-dihydro-oxazol-2-ylamine. Off-white waxy solid.

Sources & evidence

ORD record: ord-29b2be5a3e5240098e2468fcaebcd4a9
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604061B2

Reaction notes

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