Synthesis
General method: 1.08 M THF solution of borane-tetrahydrofuran complex (24.3 mL, 26.2 mmol) of 2-amino-3-methoxybenzoic acid (1.5 g, 8.74 mmol) was slowly added dropwise to a solution of tetrahydrofuran (THF, 5 mL) at 0 °C under argon protection for a controlled time of 10 min. After the dropwise addition was completed, the reaction mixture was warmed up to 30 °C and stirred continuously for 1.5 hours. After completion of the reaction, the solution was cooled to 0 °C, a mixed solution of tetrahydrofuran and water (THF/H2O = 1:1, 60 mL) and potassium carbonate was added, followed by extraction with ether three times. The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was recrystallized by ethyl acetate to give (2-amino-3-methoxy-phenyl)-methanol (1a, 1.2 g, 88% yield) as white needle-like crystals.
References
[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831
[2] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 7, p. 1193 - 1202
[3] Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 2080 - 2092
[4] Journal of Medicinal Chemistry, 2002, vol. 45, # 15, p. 3280 - 3285
[5] Angewandte Chemie - International Edition, 2016, vol. 55, # 49, p. 15272 - 15276
