Sodium triacetoxyborohydride → HCID 45378004, compound

Participants

Reaction Conditions

Reaction Steps

R-α-Methyl benzylamine (0.12 mL, 0.928 mmol) and 6-methoxy-5-(4-(trifluoromethyl)phenyl)-3-pyridinecarbaldehyde (0.261 g, 0.928 mmol) were dissolved in 3.0 mL of 1,2-dichloroethane in a 10 mL round bottom flask. The solution was allowed to stir at 25° C. for 1 h, at which point NaBH(OAc)3 (0.295 g, 1.39 mmol) was added in one portion. The reaction was then stirred for 16 h at 25° C. The reaction was quenched by adding 5N NaOH (1.5 mL) and stirring vigorously for 30 min. The layers were separated and the aqueous layer was washed with DCM (3×2.0 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated to give crude product, which was then purified by silica gel chromatography (1:1 hexane-EtOAc) to afford (1R)—N-((6-methoxy-5-(4-(trifluoromethyl)phenyl)-3-pyridinyl)methyl)-1-phenylethanamine 1. MS m/z: 387 (MH+).

Provenance & Evidence