Cyanogen Bromide → (S)-4-[3-(4-chloro-phenyl)-3-methoxy-propyl]-4,5-dihydro-oxazol-2-ylamine

HRID 1807932Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:5][CH2:6][CH:7]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[O:8][CH3:9])[CH2:3][OH:4].[N:17]#[C:18]Br>>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([CH:7]([O:8][CH3:9])[CH2:6][CH2:5][C@H:2]2[CH2:3][O:4][C:18]([NH2:17])=[N:1]2)=[CH:11][CH:12]=1

Participants

Reactant 2

HCID 10476Cyanogen Bromide

HCID 59173183(S)-2-amino-5-(4-chloro-phenyl)-5-methoxy-pentan-1-ol

Product 1

HCID 59173114(S)-4-[3-(4-chloro-phenyl)-3-methoxy-propyl]-4,5-dihydro-oxazol-2-ylamine

Procedure

In analogy to example 1d (S)-2-amino-5-(4-chloro-phenyl)-5-methoxy-pentan-1-ol was reacted with cyanogen bromide to give (S)-4-[3-(4-chloro-phenyl)-3-methoxy-propyl]-4,5-dihydro-oxazol-2-ylamine (mixture of epimers). White solid. MS (ISP): 271.2 ([{37Cl}M+H]+), 269.2 ([{35Cl}M+H]+).

Sources & evidence

ORD record: ord-ccd89576e200403f8f6bf2993e30b278
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357712B2

Reaction notes

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