Benzenemethanamine, 3-chloro-4-methoxy-.alpha.-methyl- synthesis

Yield:50460-25-8 61%

Reaction Conditions:

with ammonium acetate;sodium cyanoborohydride in methanol at 60;

Steps:

28 Example 28

Example 28: [00355] NaBH₃CN (10.52 mmol) was added to a solution of 67 (5.26 mmol) and NH₄OAc (52.6 mmol) in MeOH (15mL). The reaction mixture was stirred overnight at 60 °C and then cooled to room temperature and partitioned between AcOEt (50mL) and H₂0 (50mL). The aqueous layer was discarded and the organic phase was washed with water (2x 50mL), dried over Na₂S0₄, filtered and evaporated under reduce pressure to yield compound 68 (61 >). 1H NMR (400 MHz, CDCI₃) δ 7.37 (d, IH, J=2.0 Hz), 7.20 (dd, IH, Ji=2.0, J₂=8.4 Hz), 6.88 (d, IH, J=8.0 Hz), 4.07 (q, IH, J=6.4 Hz, CHCH₃), 3.88 (s, 3H, OCH₃), 1.84 (br s, 2H, NH₂), 1.36 (d, 3H, J=6.4 Hz, CHCH₃).

References:

WO2015/9930,2015,A2 Location in patent:Paragraph 00354-00355