Dichloromethane → HCID 53739781, compound

HRID 1417476Notes

Reaction equation

HRID 1417476 reaction equation
[H][H].[C:3]1([CH:9]2[C:21]3[NH:20][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]=3[CH2:12][CH2:11][N:10]2[CH2:22][C:23]([O:25]CC2C=CC=CC=2)=[O:24])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O1CCCC1.C(Cl)Cl>[Pd].CO>[C:3]1([CH:9]2[C:21]3[NH:20][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]=3[CH2:12][CH2:11][N:10]2[CH2:22][C:23]([OH:25])=[O:24])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 53919312HCID 53919312, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53739781HCID 53739781, compoundYield 24.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A catalytic amount of 10% w/w palladium on charcoal was added under a stream of hydrogen to a solution of 260.2 mg (0.656 mmol) of benzyl (1-phenyl-1,2,3,4-tetrahydro-β-carbolin-2-yl)acetate, as obtained in Example 71, in 2 ml each of methanol and of tetrahydrofuran, and hydrogenation was allowed to proceed for 3 hours. The palladium on charcoal catalyst was removed from the reaction mixture by filtration, and the solvent was removed by evaporation under reduced pressure to give 0.32 g of a crude mixture. The resulting residue was subjected to column chromatography using 5 g of silica gel with a 19:1 by volume mixture of methylene chloride and methanol as the eluent, to yield 0.05 g of the title compound as a pale yellow powder, melting at 157°-164° C. (with decomposition).

Workup

  1. customThe palladium on charcoal catalyst was removed from the reaction mixture by filtration
  2. customthe solvent was removed by evaporation under reduced pressure
  3. customto give 0.32 g of a crude mixture

Sources & evidence

ORD record
ord-bd9ae654088746db98564272227c35cd
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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