Acetic Acid → HCID 18600294, compound

Participants

Reaction Steps

Following the procedure of Example 1, 15.2 g of the above enamine in 150 ml of methanol were reduced with 3.78 g of sodium borohydride in 150 ml of ethanol in the presence of 5.14 ml of glacial acetic acid. The product of the reaction, trans-(±)-4-methyl-7-methoxy-3,4,4a,5,8,8a-hexahydro-2H-[1,4]benzoxazine, was hydrolysed by treatment with acid as in Example 1 to yield trans-(±)-4-methyl-3,4,4a,5,6,7,8,8a-octahydro-2H-[1,4]benzoxazin-7-one. The product was purified from a highly colored impurity by treatment with sodium bisulfite as in Example 1.

Provenance & Evidence