Heptane → HCID 11024585, compound

Participants

Reaction Conditions

Reaction Steps

In a 350 mL high pressure autoclave, 6 g (17.2 mmol) of camptothecin was suspended in 60 mL of acetic acid, and into which 2.4 g of stabilized nickel catalyst (N113) was added. After substituting the atmosphere in the autoclave with hydrogen, the suspension was heated at 110° C. under 2.0 MPa for 3 hours with stirring, whereat the starting material disappeared. The reaction liquid was cooled off to room temperature, filtered on 3 g of Celite and washed with 30 mL of acetic acid. The filtrate was washed with heptane (once with 80 mL and twice with 60 mL each), extracted with 60 mL of chloroform, and the organic layer was washed successively with 30 mL of water and 30 mL of saturated saline. The organic layer was dried over 2 g of magnesium sulfate, filtered and concentrated. To the resulting orange colored oil, 10 mL of chloroform was added and heated at 35° C. to form a homogeneous solution. Upon adding thereto 10 mL of heptane, a precipitate was formed. Distilling the solvent off under reduced pressure and drying the residue, 5.8 g of 1,2,6,7-tetrahydrocamptothecin was obtained as an orange colored powder (yield: 96.8%, in which the diastereoisomeric ratio* was 21:76).

Provenance & Evidence