Water → HCID 54370231, compound

Participants

Reaction Steps

A solution of (RS)-6-nitromethyl-7,7-diphenyl-1,4-dioxaspiro[4.5]decane (63 g) in anhydrous tetrahydrofuran (300 cc) is added dropwise in the course of 1 hour to a suspension, cooled to +5° C., of lithium aluminium hydride (8.13 g) in anhydrous tetrahydrofuran (250 cc) while the temperature of the reaction mixture is maintained at +5° C., and the mixture is then brought to reflux for 2 hours. The reaction mixture is then cooled to +5° C., treated with distilled water (8.93 cc), then with 5N aqueous sodium hydroxide solution (8 cc) and then with distilled water (25 cc), filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel with a slight excess pressure of nitrogen (0.04-0.063 mm, diameter 6.5 cm, height 45 cm), eluting with a mixture of dichloromethane and methanol (90:10) by volume) and collecting 120-cc fractions. Fractions 10 to 31 are combined and concentrated to dryness under reduced pressure (2.7 kPa). (RS)-6-Aminomethyl-7,7-diphenyl-1,4-dioxaspiro[4.5]decane (16.5 g) is obtained in the form of an orange-colored oil.

Provenance & Evidence