Sodium borohydride → N-(7-hydroxymethyl-chroman-4-yl)-3-(naphthalen-2-yl-sulfonylamino)-3-phenyl-propionamide

Participants

Reaction Conditions

Reaction Steps

N-(7-Formyl-chroman-4-yl)-3-(naphthalen-2-yl-sulfonylamino)-3-phenyl-propionamide (Example 1, Step G) (1.83 g, 3.56 mmol) was dissolved in a 1:1 solution of THF and MeOH (100 mL). The solution was cooled to 0° C. and NaBH4 (0.135 g, 3.56 mmol) was added. The reaction was stirred for 30 min. The volatiles were removed in vacuo and the resulting residue was dissolved in EtOAc and washed sequentially with a saturated NaHCO3 solution and brine. The aqueous phases were extracted once with EtOAc. The organic phases were combined, dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound. MS (ESI) m/z 517 (M+H)+.

Provenance & Evidence