반응 #1885044

반응 방정식

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

tert-butyl-N-tert-butoxycarbonyliminocarbamate

→

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

수율 99.9%

용매

THF

THF

반응 조건

후처리

1. 1
   기타the cooling bath was removed
2. 2
   온도The reaction mixture was then cooled to 0° C.
3. 3
   기타the 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
   추출extracted with EtOAc (3×)
7. 7
   세척The combined organics were washed with water (2×), brine
8. 8
   건조dried over MgSO4
9. 9
   기타evaporated to dryness
10. 10
    기타Purification by silica gel chromatography (1-10% EtOAc in hexane)

실험 절차

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.

출처