2-(aminomethyl)-6-tert-butylphenol

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: (2-fluoro-6-methoxyphenyl)methanamine was synthesized from 2-fluoro-6-methoxybenzaldehyde using a similar procedure to the described synthesis of 2-(aminomethyl)-6-tert-butylphenol.

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

Procedure: 3-tert-butyl-2-hydroxybenzaldehyde oxime (550 mg, 2.9 mmol) in EtOAc (10 mL) and MeOH (10 mL) was hydrogenated at balloon pressure in the presence of 10% Pd on carbon (100 mg) for 15 h. The reaction mixture was filtered over celite and concentrated. The residue was dissolved in EtOAc and 0.5 N HCl (10 mL). The layers were separated and the aqueous layer was treated with 1N NaOH solution until pH=9. The resulting aqueous layer was extracted with CHCl3 (3×10 mL). The combined CHCl3 was washed with brine, dried with Na2SO4 and concentrated under reduced pressure to provide to desired product (123 mg, 23%). The reaction mixture was filtered over celite and concentrated The residue was dissolved in EtOAc The layers were separated the aqueous layer was treated with 1N NaOH solution until pH=9 The resulting aqueous layer was extracted with CHCl3 (3×10 mL) The combined CHCl3 was washed with brine dried with Na2SO4 concentrated under reduced pressure