反応 #2976

反応方程式

(3R,5S)-1-t-butoxycarbonyl-5-t-butyldiphenylsiloxymethyl-3-methyl-pyrrolidine-2-one

acetic acid

tetrabutylammonium fluoride

Ethyl acetate

→

product

(3R,5S)-1-t-Butoxycarbonyl-5-hydroxymethyl-3 -methylpyrrolidine-2-one

溶媒

THF

THF

反応条件

後処理

1. 1
   抽出the organic phase extracted with aqueous ammonium chloride (20%, 3 x 200 mL)
2. 2
   抽出The combined aqueous phases were extracted with ethyl acetate (200 mL)
3. 3
   洗浄The combined organic phases were washed with brine (500 mL)
4. 4
   乾燥dried over Na2SO4
5. 5
   ろ過filtered
6. 6
   その他evaporated to dryness
7. 7
   ろ過The crude product was purified by filtration through silica gel
8. 8
   洗浄eluted with 70% EtOAc in hexane

実験手順

To a solution of (3R,5S)-1-t-butoxycarbonyl-5-t-butyldiphenylsiloxymethyl-3-methyl-pyrrolidine-2-one (17.8 g, 38.1 mmol) and glacial acetic acid (2 eq) in dry THF (50 mL) at 0° C. was added a 1.0M solution of tetrabutylammonium fluoride in THF (150 mL, 150 mmol). The solution was allowed to warm room temperature and stir overnight. Ethyl acetate (500 mL) was added and the organic phase extracted with aqueous ammonium chloride (20%, 3 x 200 mL). The combined aqueous phases were extracted with ethyl acetate (200 mL). The combined organic phases were washed with brine (500 mL), dried over Na2SO4, filtered and evaporated to dryness. The crude product was purified by filtration through silica gel, eluted with 70% EtOAc in hexane to give the product as a clear oil, which was carried on for next step without further characterization.

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