Camptothecin → HCID 11024585, compound

HRID 2069993Notes

Reaction equation

HRID 2069993 reaction equation
[CH3:1][CH2:2][C@@:3]1([OH:26])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:24](=[CH:25][C:4]1=2)[C:23]1[N:22]=[C:21]2[C:16]([CH:17]=[CH:18][CH:19]=[CH:20]2)=[CH:15][C:14]=1[CH2:13]3)=[O:11].[H][H]>C(O)(=O)C.[Ni]>[CH3:1][CH2:2][C@@:3]1([OH:26])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:24](=[CH:25][C:4]1=2)[CH:23]1[CH:14]([CH2:15][C:16]2[C:21]([NH:22]1)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13]3)=[O:11]

Participants

5

Reactant 2

HCID 24360CamptothecinHCID 178418361HCID 178418361, compound

Product 1

HCID 11024585HCID 11024585, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Procedure

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 1.2 g of stabilized nickel catalyst (N113) was added. After hydrogen substitution of the inside atmosphere, the suspension was heated at 110° C. under 2.0 MPa for 6 hours with stirring, whereat the starting material disappeared. The reaction liquid was cooled off to room temperature, filtered on 0.5 g of Celite and washed with 10 mL of acetic acid. An HPLC analysis of this solution confirmed that this Example could produce 1,2,6,7-tetrahydrocamptothecin at an yield of 97% (The diastereoisomeric ratio was 23:74).

Workup

  1. customThe reaction liquid
  2. filtrationfiltered on 0.5 g of Celite
  3. washwashed with 10 mL of acetic acid

Sources & evidence

ORD record
ord-062c98caaf79487f92bc38deb059ba9c
Source dataset
uspto-grants-2012_10
Patent number
US08299251B2

Reaction notes

Loading…