反应详情

Dimethyl (1-diazo-2-oxpropyl)phosphonate (3.90 mL, 26.0 mmol) was added to tert-butyl (2S,5S)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-formylmorpholine-4-carboxylate (Example 1, step 6) (7.78 g, 21.6 mmol) and K2CO3 (5.98 g, 43.3 mmol) in anhydrous MeOH (216 mL) at ambient temperature. The reaction was stirred for 2 hours then filtered and concentrated in vacuo. Saturated aqueous KH2PO4 was added and the mixture was extracted with ethyl acetate (×3). The combined organic fractions were dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. Purification on silica gel (750 g) eluting with a gradient of 0-30% EtOAc/hexanes afforded the title compound (4.60 g, 12.9 mmol, 60% yield) as a colorless oil, MS (ESI): m/z=256.01 (M+H-Boc).

1. filtrationthen filtered
2. concentrationconcentrated in vacuo
3. additionSaturated aqueous KH2PO4 was added
4. extractionthe mixture was extracted with ethyl acetate (×3)
5. dry with materialThe combined organic fractions were dried (MgSO4)
6. filtrationfiltered
7. customthe solvent was evaporated under reduced pressure
8. customPurification on silica gel (750 g)
9. washeluting with a gradient of 0-30% EtOAc/hexanes