Benzylamine → HCID 276585, compound

Participants

Reaction Steps

A solution of [2-[2-[(methylsulfonyl)oxy]ethyl]-5-nitrophenyl]methyl methanesulfonate (Step 1, 1.75 g, 4.95 mmol) in CH2Cl2 (25 mL) under N2 is treated with benzylamine (2.70 mL, 24.75 mmol), and the resulting mixture is stirred at ambient temperature for 24 hrs and then washed with water (20 mL) and brine (10 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product is then chromatographed on a Flash 40M silica gel (90 g, 32-63 μm) cartridge, eluting with EtOAc/heptane (10/90), and those fractions with an Rf=0.32 by TLC (EtOAc/hexane, 25/75) are pooled and concentrated to give 1.33 g (100%) of the title compound as an orange solid, mp 85-86° C.

Provenance & Evidence