Diethyl Ether → HCID 178461842, compound

Participants

Reaction Steps

To an ice cold solution of (R)-1-phenylethanamine (3.11 g, 25.7 mmol) and triethylamine (17.9 mL, 128 mmol) in dichloromethane (60 mL) was added dropwise neat titanium tetrachloride (10.7 mL, 10.7 mmol) to afford a light brown mixture. The cold bath was removed and 2,2-dimethylcyclopentanone (2.68 mL, 21.4 mmol) was added and the resulting mixture was allowed to stir at rt for ˜16 h. To this mixture was added 75 mL of diethyl ether and the resulting mixture was stirred at rt for 15 min then filtered thru a pad of Celite to remove the solids. The solids were rinsed with additional ether (30 mL×2) and the resulting clear yellow filtrate was concentrated on a rotovap to afford 4.86 g (quantitative) of the title compound as a yellow liquid. HPLC (condition B): retention time=1.58 min. LCMS (condition E): m/z 216+ve.

Provenance & Evidence