Water → HCID 15599314, compound

Participants

Reaction Steps

A solution of ethyl 2-benzylideneamino-2-methyl-4-[(tetrahydro-2H-pyran-2-yl)oxy]butyrate (67C, 100.0 g, 0.3 mol) in THF (100 mL) was added slowly to a suspension of lithium aluminum hydride (Morton Thiokol, Inc.-Alfa Products, 22.77 g, 0.6 mol) rapidly stirred in dry THF (1 L) at such a rate to maintain a gentle reflux. After the addition was complete the mixture was refluxed for 4 h. The reaction mixture was cooled and treated successively with H2O (23 mL), 15N NaOH (23 mL) and H2O (45 mL). The solid was removed by filtration and washed with THF (200 mL). The organic layers were combined and concentrated by rotary evaporation to give 2-benzylamino-2-methyl-4-[(tetrahydro-2H-pyran-2-yl)oxy]butanol (81.1 g, 92.0%) as a thick oil which was used without further purification.

Provenance & Evidence