Tetrahydro-4H-pyran-4-one → HCID 57635037, compound

Participants

Reaction Steps

To a solution of 4.904 g (0.020 mole) of (rac)-3-amino-2-methyl-propanoic acid ethyl ester trifluoroacetate in 100 mL of dichloromethane was added 2.0 g (0.02 mole) of tetrahydro-4H-pyran-4-one, 3.28 g (0.040 mole) of sodium acetate and 6.70 g (0.030 mole) of sodium triacetoxyborohydride. The mixture was stirred at room temperature for 16 hours and then 100 mL of saturated aqueous sodium bicarbonate solution (100 mL) was added. After stirring for another 30 minutes, the layers were separated. The aqueous layer was extracted twice with 100 mL of dichloromethane. The organic layers were washed with 100 mL of brine, combined, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was distilled under vacuum to give 2.05 g of (rac)-2-methyl-3-(tetrahydro-pyran-4-ylamino)-propanoic acid ethyl ester as colorless oil. b.p. 135° C., 8 mm Hg.

Provenance & Evidence