2,2-Dimethylcyclopentanone → HCID 57635070, compound

Participants

Reaction Steps

To a solution of 13.8 g (0.090 mole) of 3-amino-propanoic acid ethyl ester HCl salt and 10.0 g (0.090 mole) of 2,2-dimethyl-cyclopentanone in 500 mL of dichloromethane was added 16.4 g (0.198 mole) of sodium acetate and 28.6 g (0.135 mole) of sodium triacetoxyborohydride. The mixture was stirred at ambient temperature overnight and then quenched by the addition of 100 mL of 10% sodium bicarbonate solution. The aqueous layer was extracted twice with 300 mL of dichloromethane, and the combined dichloromethane layers dried over anhydrous magnesium sulfate. The mixture was filtered, concentrated under reduced pressure, and distilled at 0.0015 mm Hg (bp 75 degrees), to give 15.4 g of (rac)-3-(2,2-dimethyl-cyclopentylamino)-propanoic acid ethyl ester.

Provenance & Evidence