Acetic Acid → HCID 21959504, compound

Participants

Reaction Steps

To a stirred solution of aldehyde (509 mg, 2.4 mmol, Step B) and morpholine (0.21 mL, 2.4 mmol) in THF (30 mL) was added NaBH(OAc)3 (0.73 g, 3.4 mmol). The mixture was stirred at RT overnight and washed with HCl (1 M). CH2Cl2 was added and the layers were separated. The aqueous layer was basified to pH 9 using NaOH 1M and extracted with CH2Cl2. The organic layer was dried and evaporated the nitro compound. To a solution of the nitro compound (0.50 g, 1.8 mmol) in THF (40 mL) was added AcOH (1.97 mmol, 34.5 mmol) followed by zinc (9.1 g, 137 mmol). The mixture was stirred for 1 h, filtered on Celite®, diluted with water and aqueous NaHCO3, and the THF layer was evaporated. The residue was extracted with EtOAc, dried and evaporated to give the title compound.

Provenance & Evidence