反应详情

DIPEA (1.801 gm, 13.94 mmol) was slowly added to a 0° C. mixture of (S)-2-(tert-butoxycarbonylamino)pent-4-enoic acid (1.00 gm, 4.65 mmol), (R)-2-vinylpiperidine hydrochloride (0.720 gm, 4.88 mol), EDC (1.02 gm, 5.34 mmol) and HOBt (0.818 gm, 5.34 mmol) in DCM (19 mL). The yellow reaction mixture was then stirred at rt for 3 days. The reaction mixture was concentrated to remove the DCM and the residue was partitioned between EtOAc and 0.5 N aqueous HCl. The organic phase was isolated, washed with saturated aqueous NaHCO3 and saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. The crude product was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-100% EtOAc/Hex to give tert-butyl (S)-1-oxo-1-((R)-2-vinylpiperidin-1-yl)pent-4-en-2-ylcarbamate (1.00 gm, 3.24 mmol, 69.8% yield) as a colorless oil. Anal. Calcd. for C17H28N2O3 m/z 308.3. found: 309.0 (M+H)+.

1. concentrationThe reaction mixture was concentrated
2. customto remove the DCM
3. customthe residue was partitioned between EtOAc and 0.5 N aqueous HCl
4. customThe organic phase was isolated
5. washwashed with saturated aqueous NaHCO3 and saturated aqueous NaCl
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe crude product was purified
10. washeluting with a gradient of 0-100% EtOAc/Hex