Ammonium Acetate → 1450660-63-5

To a solution of 1-(4,4-difluorocyclohexyl)ethanone (1 g, 6.17 mmol) in THF (5 mL) was added a solution of ammonium acetate (9.51 g, 123.4 mmol) and NaBH3CN (3.82 g, 61.7 mmol) in MeOH. The mixture was stirred for 48 hr. The reaction mixture was quenched with aqueous NaHCO3 and extracted with tert-Butyl-methyl ether (20 mL*3). The combined organic layers were washed with 1N HCl, and the organic and aqueous layer were separated. The aqueous layer was brought to above pH 8 with 2N NaOH and extracted with ethyl acetate (20 mL*3). The organic layer was washed with brine, dried over sodium sulfate. The organic layer was concentrated to give 1-(4,4-difluorocyclohexyl)ethanamine (545 mg, crude) for next step.

1. customThe reaction mixture was quenched with aqueous NaHCO3
2. extractionextracted with tert-Butyl-methyl ether (20 mL*3)
3. washThe combined organic layers were washed with 1N HCl
4. customthe organic and aqueous layer were separated
5. extractionextracted with ethyl acetate (20 mL*3)
6. washThe organic layer was washed with brine
7. dry with materialdried over sodium sulfate
8. concentrationThe organic layer was concentrated

ORD record

ord-596f4c590ea648d0800b9662e611f104

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371331B2