反応 #1885045

反応方程式

water

(3R)-3-(tert-butyldiphenylsilyloxy)-1-phenylpyrrolidin-2-one

TBAF

→

(R)-3-hydroxy-1-phenylpyrrolidin-2-one

溶媒

THF

反応条件

後処理

1. 1
   抽出extracted with EtOAc (3×)
2. 2
   乾燥The combined organics were dried over Na2SO4
3. 3
   その他evaporated to dryness
4. 4
   その他Purification by silica gel chromatography (0-10% MeOH in DCM)

実験手順

To a solution of (3R)-3-(tert-butyldiphenylsilyloxy)-1-phenylpyrrolidin-2-one (2.88 g, 6.93 mmol) in THF (8.6 mL) at 0° C. was added TBAF (13.9 mL of 1 M in THF, 13.86 mmol) slowly and the reaction mixture was stirred at RT for 3 h. The reaction mixture was poured into water and extracted with EtOAc (3×). The combined organics were dried over Na2SO4 and evaporated to dryness. Purification by silica gel chromatography (0-10% MeOH in DCM) gave (R)-3-hydroxy-1-phenylpyrrolidin-2-one as a white solid (0.9 g 73%). 1H-NMR (400 MHz, DMSO-d6) δ 7.69 (d, J=7.8 Hz, 2H), 7.40-7.36 (m, 2H), 7.14 (t, J=7.4 Hz, 1H), 5.75 (d, J=5.8 Hz, 1H), 4.33-4.27 (m, 1H), 3.77-3.66 (m, 2H), 2.44-2.36 (m, 1H) and 1.86-1.81 (m, 1H) ppm.

出典