Methanol → (S)-2-(tert-Butyl-dimethyl-silanyloxy)-propan-1-ol

Temperature

0 °C

A 2M solution of LiBH4 (2.77 g, 0.13 mol) in THF (60 mL) was added dropwise to a solution of (S)-2-(tert-butyl-dimethyl-silanyloxy)-propionic acid ethyl ester (22.75 g, 0.10 mol) and methanol (5.15 mL, 0.13 mol) in diethyl ether (500 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour and then at room temperature for 1.5 hours before cooling to 0° C. and carefully quenching with water. The reaction mixture was filtered and the filtrate extracted with diethyl ether (2×50 mL), the combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to give the title product as a colourless oil (18.2 g, 97%). 1H NMR (CDCl3, 400 MHz) 3.86-3.77 (1H, m), 3.45-3.37 (1H, m), 3.31-3.22 (1H, m), 1.96-1.85 (1H, m), 1.03 (3H, d, J=6.23 Hz), 0.81 (9H, s), 0.00 (6H, s).

1. temperatureat room temperature for 1.5 hours before cooling to 0° C.
2. customcarefully quenching with water
3. filtrationThe reaction mixture was filtered
4. extractionthe filtrate extracted with diethyl ether (2×50 mL)
5. washthe combined organic extracts were washed with brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo

ORD record

ord-5d1588e0d71540deab4e0632e43c9069

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841462B2