Sodium borohydride → HCID 21961470, compound

Participants

Reaction Steps

1-Methyl-4-[1-methyl-1-(4-nitro-phenyl)-ethyl]-pyridinium (Step A) was treated with DEA (100 mL) in MeOH (300 mL) for 2 h. NaBH4 (19 g, 500 mmol) was added in small portions. The resulting mixture was stirred for 30 min at RT, then partitioned between CH2Cl2/H2O (500 mL/500 mL). The organic layer was collected and the upper layer was washed with CH2Cl2 (300 mL×3). The combined organic layer was washed with brine then concentrated in vacuo. The residue was purified on a silica washed-column (7% TEA in EtOAc). The desired fractions were combined and concentrated under vacuum to give the desired compound as a dark gray solid. (MS: M+1=261).

Provenance & Evidence