反应 #1885044

反应方程式

(R)-2-(tert-butyldiphenylsilyloxy)-4-hydroxy-N-phenylbutanamide

tert-butyl-N-tert-butoxycarbonyliminocarbamate

→

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

收率 99.9%

溶剂

THF

THF

反应条件

后处理

1. 1
   其他the cooling bath was removed
2. 2
   温度The reaction mixture was then cooled to 0° C.
3. 3
   其他the cooling bath removed
4. 4
   workup.STIRRINGthe reaction mixture stirred at RT for 45 min
5. 5
   workup.ADDITIONThe reaction mixture was poured into water
6. 6
   萃取extracted with EtOAc (3×)
7. 7
   洗涤The combined organics were washed with water (2×), brine
8. 8
   干燥dried over MgSO4
9. 9
   其他evaporated to dryness
10. 10
    其他Purification by silica gel chromatography (1-10% EtOAc in hexane)

实验过程

To a solution of tert-butyl-N-tert-butoxycarbonyliminocarbamate (2.44 g, 10.61 mmol) in THF (17.25 mL) at 0° C. was added n-tributylphosphine (2.15 g, 2.64 mL, 10.61 mmol) dropwise, the cooling bath was removed and the reaction mixture stirred at RT for 20 min. The reaction mixture was then cooled to 0° C. and a solution of (R)-2-(tert-butyldiphenylsilyloxy)-4-hydroxy-N-phenylbutanamide (1.15 g, 2.65 mmol) in THF (17.25 mL) was added slowly, the cooling bath removed and the reaction mixture stirred at RT for 45 min. The reaction mixture was poured into water and extracted with EtOAc (3×). The combined organics were washed with water (2×), brine, dried over MgSO4 and evaporated to dryness. Purification by silica gel chromatography (1-10% EtOAc in hexane) afforded (R)-3-(tert-butyldiphenylsilyloxy)-1-phenylpyrrolidin-2-one (1.1 g, 96%) as an oil. 1H-NMR (400 MHz, DMSO-d6) δ 7.81 (dd, J=1.5, 7.7 Hz, 2H), 7.72-7.66 (m, 4H), 7.51-7.36 (m, 8H), 7.15 (m, 1H), 4.51 (dd, J=8.1, 9.2 Hz, 1H), 3.72-3.59 (m, 2H), 2.26-2.21 (m, 1H), 2.03-1.98 (m, 1H) and 1.06 (s, 9H) ppm. LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=416.7; tR=2.40 min.

来源