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

HRID 1026116Notes

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-6eea0087f0ee481da98ea32320fd8ba0
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729113B2

Reaction notes

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