(3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile

Description

(3S)-4-Chloro-3-[(trimethylsilyl)oxy]butanenitrile, also known as (3S)-4-Chloro-3-[(trimethylsilyl)oxy]butanenitrile, is a useful research compound.  Its molecular formula is C7H14ClNOSi and its molecular weight is 191.73 g/mol. The purity is usually 95%.

Uses

(3S)-4-Chloro-3-[(trimethylsilyl)oxy]butanenitrile is used in the synthesis of statins or HMG-CoA reductase inhibitors.

Synthesis

The synthesis of (3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile is as follows:
To a solution of (S)-4-chloro-3-hydroxy butanenitrile (52.5 g) in THF (150 mL) was added trimethyl silyl chloride (57.2 g) under inert atmosphere at 25 °C. The resulting reaction mixture was stirred for 10 min at 20°C. A solution of triethyl amine (53.4 g) in THF (100 mL) was added to above reaction mixture by maintaining reaction temperature below 40 °C. To the resulting reaction mixture catalytic amount of sodium iodide was added and stirred further for 5 h at 40°C. Reaction was monitored on GC as well TLC for complete conversion of starting material. After cooling to 0 °C, a 21% aqueous solution of sodium chloride (500 mL) was added and extracted with ethyl acetate (2 X 300 mL). Combined organic layer was dried with anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain (3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile as light brown liquid (84.0 g, 99%).