Dicyclohexylcarbodiimide → HCID 22600031, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-ylamine (1) (0.5 g, 2.46 mmole) in 25 mL of dichloromethane was cooled to 0° C. and was successively treated with ethoxyacetic acid (0.26 mL, 1.1 eq.), dimethylaminopyridine (30 mg, 0.1 eq.) and dicyclohexylcarbodiimide (560 mg, 1.1 eq.). The reaction mixture was stirred at 0° C. for two hours then at room temperature for two hours, diluted with 25 mL water and extracted with three 25 mL portions of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo. The resulting solid/oil was triturated in ether, the solid removed and the volatiles removed in vacuo, to give 674 mg (95%) of 2-ethoxy-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide (35) as a pale yellow solid, which was used without purification.

Provenance & Evidence