201932-92-5

The general procedure for the synthesis of methyl 3-(hydroxymethyl)-4-nitrobenzoate from methyl 3-formyl-4-nitrobenzoate was as follows:(RS-3-49) Methyl 3-formyl-4-nitrobenzoate (1.20 g, 5.73 mmol) was dissolved in methanol (10 mL) and the solution was cooled to 0 °C. Sodium borohydride (69 mg, 1.72 mmol) was added all at once under stirring and the reaction mixture continued to be stirred at 0 °C for 20 min. Upon completion of the reaction, the reaction was quenched with 1N hydrochloric acid (10 mL) followed by evaporation under reduced pressure to remove methanol. The remaining aqueous phase was extracted with dichloromethane (3 x 10 mL) and the organic phases were combined, dried over anhydrous sodium sulfate and concentrated to afford the crude product methyl 3-(hydroxymethyl)-4-nitrobenzoate (1.06 g), which could be used in the subsequent reaction without further purification.

[1] Patent: WO2014/131023, 2014, A1. Location in patent: Page/Page column 138
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 4812 - 4830