反应详情

温度

-20 °C

4-(4-Cyano-3-methylphenyl)tetrahydro-2H-thiopyran-4-carbonitrile (983 mg, 4.06 mmol) is stirred in THF (40.0 mL) at −78° C. under nitrogen as a 1.6 M solution of methyllithium in Et2O is added slowly via syringe to the vessel. The contents are stirred for 3 hours at −20° C. before being quenched with MeOH (40.0 mL) and warmed to room temperature. NaBH4 (460 mg, 12.2 mmol) is slowly added at 0° C. in an ice bath and the mixture is warmed to room temperature and stirred for 16 hours. 1.0 N aqueous HCl is added until a pH of 3.0 is reached and the solvent is removed by rotary evaporator. To the residue is added concentrated aqueous HCl (3.0 mL) and the mixture is stirred for 16 hours. The contents are neutralized with 1.0 M aqueous NaOH and EtOAc (40.0 mL) is added. The layers are separated and the organic is dried with Na2SO4 and concentrated to a residue that is purified by silica get column chromatography (10% MeOH in DCM) (253 mg, 1.05 mmol, 26%).

1. additionis added slowly via syringe to the vessel
2. custombefore being quenched with MeOH (40.0 mL)
3. temperaturewarmed to room temperature
4. temperaturethe mixture is warmed to room temperature
5. stirringstirred for 16 hours
6. customthe solvent is removed by rotary evaporator
7. additionTo the residue is added concentrated aqueous HCl (3.0 mL)
8. stirringthe mixture is stirred for 16 hours
9. additionis added
10. customThe layers are separated
11. dry with materialthe organic is dried with Na2SO4
12. concentrationconcentrated to a residue that
13. customis purified by silica
14. customget column chromatography (10% MeOH in DCM) (253 mg, 1.05 mmol, 26%)