Tert-Butylamine → HCID 15711867, compound

Participants

Reaction Conditions

Reaction Steps

Bromine (0.11 mL, 2.1 mmol) was added to a solution of 0.91 mL (8.7 mmol) of t-butylamine in 15 mL of toluene at 31 30° C. The resultant mixture was stirred at -30° C. for 10 minutes, cooled to -78° C. and then treated with a solution of 1.09 g (4.3 mmol) of 1-cyano-3,4-dihydro -5-hydroxy-3-phenyl-1H-2-benzopyran, from Step 3, in 15 mL of methylene chloride. The reaction mixture was stirred at -78° C. for 3 h, allowed to slowly warm to ambient temperature over a 3 h period and then partitioned between ethyl acetate and water. The organic extract was washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel eluted with 1% ethyl acetate in hexane to give 0.32 g (24% yield) of [1 R, 3 R]-6-bromo-1-cyano-3,4-dihydro-5-hydroxy-3-phenyl-1H-2-benzopyran and 0.26 g (20% yield) of [1R,3S] 6-bromo-1-cyano-3,4-dihydro-5-hydroxy-3-phenyl-1H-2-benzopyran.

Provenance & Evidence