反应详情

Add sodium cyanoborohydride (3.36 g, 53.5 mmol) to a solution of 4-cyanobenzaldehyde (1.75 g, 13.35 mmol) and (R)-1-methyl-2,2,2-trifluoro-ethylamine hydrochloride (2 g, 13.37 mmol) in methanol (17 mL) containing acetic acid (1.53 mL, 26.75 mmol). Stir the mixture at room temperature overnight. Partition the mixture between 1N aqueous NaOH/DCM (1:1, 500 mL) and extract the aqueous layer twice with DCM. Dry the combined organic extracts over MgSO4, concentrate in vacuo and purify by chromatography on silica gel (120 g) eluting with hexane/EtOAc (19:1, 9:1, 85:15 and 4:1) to obtain the desired intermediate (0.83 g, 27%). MS (ES+) m/z: 229 (M+H)+.

1. customPartition the mixture between 1N aqueous NaOH/DCM (1:1, 500 mL)
2. extractionextract the aqueous layer twice with DCM
3. dry with materialDry the combined organic extracts over MgSO4
4. concentrationconcentrate in vacuo
5. custompurify by chromatography on silica gel (120 g)
6. washeluting with hexane/EtOAc (19:1, 9:1, 85:15 and 4:1)