Pyridine → HCID 56619428, compound

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Reaction Steps

11.24 g of (3S)-2-benzyloxycarbonyl-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline are dissolved in 40 ml of pyridine. 7.01 g of p-toluenesulfonyl chloride are added dropwise to the mixture of 5° C., and the mixture is stirred at the same temperature for 30 minutes. The mixture is evaporated under reduced pressure to remove the solvent. The residue is dissolved in ethyl acetate, and the solution is washed with 5% HCl and water, dried and then evaporated to remove the solvent. The residue is dissolved in 50 ml of dimethylformamide, and the solution is added dropwise to a suspension of 2.21 g of sodium cyanide in 40 ml of dimethylformamide. The addition is carried out at 5° C. The mixture is stirred at the same temperature for 2 hours, and then at room temperature for 60 hours. The mixture is evaporated under reduced pressure to remove the solvent. Water is added to the residue, and the aqueous solution is extracted with ethyl acetate. The extract is washed with water, dried and then evaporated to remove the solvent. The residue is purified by silica gel column chromatography (Solvent; ethyl acetate:n-hexane=1:2). 3.78 g of (3S)-2-benzyloxycarbonyl-3-cyanomethyl-1,2,3,4-tetrahydro-β-carboline are obtained as pale red oil. Yield: 36%

Provenance & Evidence