反应详情

To a solution of the product of Step E (255.9 g, 1.01 mol) and MeOH (2 L) chilled to 2° C. was added NaBH4 (75 g) over ˜2.5 h. The reaction was quenched by addition of aqueous NH4Cl, concentrated under reduced pressure and the mixture was diluted with water and EtOAc. The layers were separated and the aqueous layer was extracted with additional EtOAc. The combined organics were washed with brine, dried (MgSO4) and evaporated to give the product of Step F as a thick oil. 1H NMR (400 MHz, CHLOROFORM-d) d=5.74 (d, J=2.0 Hz, 2H), 4.81-4.92 (m, 1H), 4.67-4.79 (m, 1H), 3.71 (t, J=6.1 Hz, 2H), 3.50 (d, J=11.7 Hz, 2H), 2.14-2.28 (m, 2H), 1.70 (td, J=1.6, 6.2 Hz, 4H), 1.52-1.60 (m, 1H), 1.44 (s, 9H)

1. customThe reaction was quenched by addition of aqueous NH4Cl
2. concentrationconcentrated under reduced pressure
3. additionthe mixture was diluted with water and EtOAc
4. customThe layers were separated
5. extractionthe aqueous layer was extracted with additional EtOAc
6. washThe combined organics were washed with brine
7. dry with materialdried (MgSO4)
8. customevaporated