反应详情

To a stirred suspension of cis-4-hydroxycyclohexanecarboxylic acid (1.0 g, 6.94 mmol), benzylamine (0.82 mL, 7.51 mmol) and HOAt (1.0 g, 7.35 mmol) in dichloromethane (50 mL) was added EDC free base (1.2 g, 7.73 mmol). The reaction was stirred overnight at room temperature, at which time it was washed with 1 N HCl, 1 N Na2CO3, brine, dried (MgSO4), filtered and concentrated under vacuum. Purification by silica gel chromatography (Analogix, SF25-80 g, 0 to 4% MeOH in CH2Cl2) gave (cis)-N -benzyl-4-hydroxycyclohexanecarboxamide (1.0 g, 4.29 mmol, 61.8% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.20 (t, J=5.81Hz, 1H), 7.26-7.38 (m, 2H), 7.11-7.27 (m, 3H), 4.31 (d, J=3.28 Hz, 1H), 4.25 (d, J=6.06 Hz, 2H), 3.76 (d, J=2.53 Hz, 1H), 2.08-2.22 (m, 1H), 1.73-1.89 (m, 2H), 1.56-1.69 (m, 2H), 1.33-1.49 (m, 4H). MS(ES) [M+H]+ 234.0.

1. washwas washed with 1 N HCl, 1 N Na2CO3, brine
2. dry with materialdried (MgSO4)
3. filtrationfiltered
4. concentrationconcentrated under vacuum
5. customPurification by silica gel chromatography (Analogix