Reacción #1885044

Ecuación de reacción

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

tert-butyl-N-tert-butoxycarbonyliminocarbamate

→

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

Rendimiento 99.9%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe cooling bath was removed
2. 2
   TemperaturaThe reaction mixture was then cooled to 0° C.
3. 3
   Otrothe 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
   Extracciónextracted with EtOAc (3×)
7. 7
   LavadoThe combined organics were washed with water (2×), brine
8. 8
   Secadodried over MgSO4
9. 9
   Otroevaporated to dryness
10. 10
    OtroPurification by silica gel chromatography (1-10% EtOAc in hexane)

Procedimiento

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.

Fuente