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

HRID 885166Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8])[CH2:3][OH:4].C([O-])(=O)C.[Na+].[N:20]#[C:21]Br>CO>[C:9]1([CH:7]([CH3:8])[CH2:6][CH2:5][C@H:2]2[CH2:3][O:4][C:21]([NH2:20])=[N:1]2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of (2S)-2-amino-5-phenyl-hexan-1-ol (160 mg) in methanol (11 ml) at room temperature was added sodium acetate (136 mg). The mixture was cooled to 0° C. and a solution of cyanogen bromide (96 mg) in methanol (2 ml) was added dropwise. The mixture was stirred at 0° C. for 30 min and then at room temperature overnight before being concentrated in vacuo. The residue was resuspended in tetrahydrofuran/ethyl acetate (1/2) and washed sequentially with saturated aqueous sodium bicarbonate solution and saturated brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (SiO2, heptane/dichloromethane/methanol gradient; eluant containing 1% aq. ammonia) to yield a colourlessoil, (128 mg, 71%); MS (ISP): 219.2 ([M+H]).

Workup

concentrationat room temperature overnight before being concentrated in vacuo
washwashed sequentially with saturated aqueous sodium bicarbonate solution and saturated brine
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (SiO2, heptane/dichloromethane/methanol gradient; eluant containing 1% aq. ammonia)
customto yield a colourlessoil, (128 mg, 71%)

Sources & evidence

ORD record: ord-010cb5b69ce143d88cebe8659c047617
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242153B2

Reaction notes

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