Dimethyl Sulfoxide → HCID 11742180, compound

Participants

Reaction Steps

methylene chloride (50 ml) is added dropwise at -78° C. a solution of dimethyl sulfoxide (2.86 g) in methylene chloride (20 ml). The mixture is stirred for 10 minutes. To the resulting reaction mixture is added dropwise a solution of 1-tertbutoxycarbonyl-4-(3,4,5-trimethoxybenzoyl)piperazine-2-methanol (5.0 g) obtained in Reference Example 4 in methylene chloride (10 ml). The mixture is stirred for 20 minutes. To the mixture is added triethylamine (7.4 g), followed by raising the reaction temperature up to room temperature. The reaction mixture is poured into ice water, followed by extraction with methylene chloride. The organic layer is washed with water, dried and concentrated under reduced pressure. The concentrate is recrystallized from ethyl acetate to give 1-tert-butoxycarbonyl-4-(3,4,5-trimethoxybenzoyl)piperazine-2-carbaldehyde as colorless prisms (4.1 g), m.p. 160-161° C.

Provenance & Evidence