Aluminium lithium hydride → (2S)-2-amino-3-butyl-1-heptanol

Temperature

36 °C

To a slurry of LAH (1.219 g, 32.13 mmol) in THF (60 mL) was added (4R)-3-[(2S)-2-azido-3-butylheptanoyl]-4-benzyl-1,3-oxazolidin-2-one (3.6 g, 9.37 mmol) dropwise at 0° C. over 20 min. The reaction was heated to 36° C. for 18 h. The reaction slurry (brown) was cooled to 0° C. and the reaction was quenched with H2O (15 mL) and washed with 1N NaOH (30 mL) and H2O (15 mL). It was let stir for 2 h to obtain an off-white slurry. The slurry was filtered and the mother liquor was further dried over MgSO4, filtered, and concentrated in vacuo to obtain (2S)-2-amino-3-butyl-1-heptanol as a crude yellow oil (1.93 g, 73.75%). Mass Spectrum (+ESI): 188 (M+H)+.

1. temperatureThe reaction slurry (brown) was cooled to 0° C.
2. customthe reaction was quenched with H2O (15 mL)
3. washwashed with 1N NaOH (30 mL) and H2O (15 mL)
4. customto obtain an off-white slurry
5. filtrationThe slurry was filtered
6. dry with materialthe mother liquor was further dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-bf51a2634d5e4adf826fde9a6e8f653b

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07691884B2