Pyridine → HCID 56619428, compound

HRID 1732139Notes

Reaction equation

HRID 1732139 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@H:23]([CH2:24]O)[CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[N:37]1C=CC=C[CH:38]=1>>[CH2:1]([O:8][C:9]([N:11]1[C@H:23]([CH2:24][C:38]#[N:37])[CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 70455602HCID 70455602, compound

Product 1

HCID 56619428HCID 56619428, compoundYield 36%

Procedure

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%

Workup

  1. customThe mixture is evaporated under reduced pressure
  2. customto remove the solvent
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washthe solution is washed with 5% HCl and water
  5. customdried
  6. customevaporated
  7. customto remove the solvent
  8. dissolutionThe residue is dissolved in 50 ml of dimethylformamide
  9. additionthe solution is added dropwise to a suspension of 2.21 g of sodium cyanide in 40 ml of dimethylformamide
  10. additionThe addition
  11. customis carried out at 5° C
  12. stirringThe mixture is stirred at the same temperature for 2 hours
  13. waitat room temperature for 60 hours
  14. customThe mixture is evaporated under reduced pressure
  15. customto remove the solvent
  16. additionWater is added to the residue
  17. extractionthe aqueous solution is extracted with ethyl acetate
  18. washThe extract is washed with water
  19. customdried
  20. customevaporated
  21. customto remove the solvent
  22. customThe residue is purified by silica gel column chromatography (Solvent; ethyl acetate:n-hexane=1:2)

Sources & evidence

ORD record
ord-d57d45cad5ee4434935c8e57fb258bb9
Source dataset
uspto-grants-1986_11
Patent number
US04625032

Reaction notes

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