2-(2,2-difluoroethylamino)ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Borane-tetrahydrofuran complex (40 ml of a 1.0 N solution in THF, 40 mmol) was added dropwise at 0° C. to a solution of 2,2-difluoro-N-(2-hydroxyethyl)acetamide (2.78 g, 20 mmol) in tetrahydrofuran (30 ml). The mixture was warmed to ambient temperature and then heated at reflux for 18 hours. The reaction mixture was cooled to ambient temperature and concentrated hydrochloric acid (6 ml) was added dropwise. The solvent was evaporated and the crude product was purified by chromatography on silica gel. Elution with dichloromethane:methanolic ammonia (96:4) then dichloromethane:methanolic ammonia (94:6) yielded 2-((2,2-difluoroethyl)amino)ethanol (0.97 g, 39% yield): heated at reflux for 18 hours The reaction mixture was cooled to ambient temperature The solvent was evaporated the crude product was purified by chromatography on silica gel Elution with dichloromethane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Borane-tetrahydrofuran complex (40 ml of a 1.0 N solution in THF, 40 mmol) was added dropwise at 0° C. to a solution of 2,2-difluoro-N-(2-hydroxyethyl)acetamide (2.78 g, 20 mmol) in tetrahydrofuran (30 ml). The mixture was warmed to ambient temperature and then heated at reflux for 18 hours. The reaction mixture was cooled to ambient temperature and concentrated hydrochloric acid (6 ml) was added dropwise. The solvent was evaporated and the crude product was purified by chromatography on silica gel. Elution with dichloromethane:methanolic ammonia (96:4) then dichloromethane:methanolic ammonia (94:6) yielded 2-((2,2-difluoroethyl)amino)ethanol (0.97 g, 39% yield): heated at reflux for 18 hours The reaction mixture was cooled to ambient temperature The solvent was evaporated the crude product was purified by chromatography on silica gel Elution with dichloromethane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Borane-tetrahydrofuran complex (40 ml of a 1.0 N solution in THF, 40 mmol) was added dropwise at 0° C. to a solution of 2,2-difluoro-N-(2-hydroxyethyl)acetamide (2.78 g, 20 mmol) in tetrahydrofuran (30 ml). The mixture was warmed to ambient temperature and then heated at reflux for 18 hours. The reaction mixture was cooled to ambient temperature and concentrated hydrochloric acid (6 ml) was added dropwise. The solvent was evaporated and the crude product was purified by chromatography on silica gel. Elution with dichloromethane:methanolic ammonia (96:4) then dichloromethane:methanolic ammonia (94:6) yielded 2-((2,2-difluoroethyl)amino)ethanol (0.97 g, 39% yield): heated at reflux for 18 hours The reaction mixture was cooled to ambient temperature The solvent was evaporated the crude product was purified by chromatography on silica gel Elution with dichloromethane