Dimethylformamide → HCID 11500672, compound

Participants

Reaction Steps

(7-Benzenesulfonyl-chroman-4-yl)-acetonitrile (397 mg, 1.26 mmol) was dissolved in 5 mL THF, and 190 ul (1.9 mmol) of BH3.DMF was added. The reaction mixture was heated to reflux for one hour and then cooled to room temperature, quenched by addition of methanol, and diluted with water. The aqueous mixture was extrated with EtOAc. The organic phase was dried over MgSO4, and solvent was removed under reduced pressure. The residue was chromatographed through silica gel (MeOH:CH2Cl2:NH4OH 8%:90%:2%), and solvent was removed under reduced pressure to yield 120 mg (0.38 mmol, 30%) of 2-(7-benzenesulfonyl-chroman-4-yl)-ethylamine. This product was dissolved in 2N HCl/EtOH and recrystallized by addition of Et2O to afford 95 mg of the corresponding hydrochloride salt. Mp: 244.6-245.8° C.

Provenance & Evidence