Methanol → HCID 13657796, compound

Participants

Reaction Conditions

Reaction Steps

In a 1 l flask, equipped with thermometer and mechanical stirrer, in a nitrogen atmosphere are added: 71.55 g (0.272 mol) of raw 3-benzyl-5-hydroxymethyl-5-carboxyethyl isoxazoline deriving from Example 3 and 553 ml of methanol. The solution is cooled to −10° C. and in the time period of 1 h are added: 10.29 g (0.272 mol) of NaBH4 granules (10–40 mesh). Once the addition is completed the temperature is increased up to room temperature and the solution is allowed to stir for 1 h 30′. Then are added 250 ml of a saturated ammonium chloride solution maintaining the temperature at approx. 20° C. The solvent is evaporated under vacuum (24 mbar at 25° C.). The residue is taken up with 150 ml of methylene chloride and the residue formed after evaporation is dissolved in a minimum quantity of water. The two phases obtained are separated and the aqueous one is retroextracted three times, each time with a volume of 100 ml, with methylene chloride. The organic phases are collected and dried with sodium sulphate. It is filtered and, after evaporation of the solvent, 59.85 g of a raw orange oil product are obtained. The raw product is crystallized in 150 ml of ethyl acetate and 140 ml of hexane. 39.91 g of 3-benzyl-5,5-bis(hydroxymethyl)isoxazoline as a pale yellow solid are obtained. Another 4.16 g of product are recovered from the mother liquors.

Provenance & Evidence