Aluminium lithium hydride → (2S,4S)-2-amino-4-phenylhexan-1-ol

To a suspension of lithium aluminum hydride (121 mg, 3.18 mmol) in tetrahydrofuran (8 ml) was added a solution of (2S,4S)-2-amino-4-phenyl-hexanoic acid methyl ester (320 mg, 1.45 mmol) in tetrahydrofuran (10 ml) and the mixture was stirred for 16 hours. The reaction was quenched by dropwise addition of ethyl acetate, then acidified to pH 5 by addition of hydrochloric acid and then made basic by addition of saturated aqueous sodium bicarbonate solution. The mixture was taken up in ethyl acetate/tetrahydrofuran (1:1), the phases were separated and the organic phase was washed sequentially with water and with saturated brine. The organic phase was then dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: dichloromethane/MeOH) to yield a yellow oil, (116 mg, 42%); MS (ISP): 194.4 ([M+H]+).

1. customThe reaction was quenched by dropwise addition of ethyl acetate
2. additionacidified to pH 5 by addition of hydrochloric acid
3. additionmade basic by addition of saturated aqueous sodium bicarbonate solution
4. customthe phases were separated
5. washthe organic phase was washed sequentially with water and with saturated brine
6. dry with materialThe organic phase was then dried over Na2SO4
7. concentrationconcentrated in vacuo
8. customThe residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: dichloromethane/MeOH)
9. customto yield a yellow oil, (116 mg, 42%)

ORD record

ord-271b92533ecd4e8faaf0cbd0b9c6e95f

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09132136B2