Cyanogen Bromide → (S)-4-[2-(4-chloro-phenoxy)-ethyl]-4,5-dihydro-oxazol-2-ylamine

HRID 1807889Notes

Reaction equation

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

Participants

Reactant 2

HCID 10476Cyanogen Bromide

HCID 57191497(S)-2-amino-4-(4-chloro-phenoxy)-butan-1-ol

Product 1

HCID 45102232(S)-4-[2-(4-chloro-phenoxy)-ethyl]-4,5-dihydro-oxazol-2-ylamine

Procedure

In analogy to example 1d (S)-2-amino-4-(4-chloro-phenoxy)-butan-1-ol was reacted with cyanogen bromide to give (S)-4-[2-(4-chloro-phenoxy)-ethyl]-4,5-dihydro-oxazol-2-ylamine. White solid. MS (ISP): 240.9 ([M+H]+))

Sources & evidence

ORD record: ord-3bf70641f45746e2a937f25298a5d191
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357712B2

Reaction notes

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