4-(4-Vinyl-5-isoquinolyl)amino-1-(tert-butoxycarbonyl)piperidine → 4-(4-Ethyl-5-isoquinolyl)amino-1-(tert-butoxycarbonyl)piperidine

HRID 10540Notes

Reaction equation

HRID 10540 reaction equation
[CH:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH:6]=[N:5][CH:4]=1)=[CH2:2]>CO.[C].[Pd]>[CH2:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:16][CH2:15]2)[CH:6]=[N:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 219799424-(4-Vinyl-5-isoquinolyl)amino-1-(tert-butoxycarbonyl)piperidine

Product 1

HCID 219798934-(4-Ethyl-5-isoquinolyl)amino-1-(tert-butoxycarbonyl)piperidineYield 90.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A solution (2 ml) of Intermediate 81 (103 mg) in methanol was vigorously stirred in the presence of 10% palladium carbon catalyst (16.5 mg) at room temperature under hydrogen atmosphere of ordinary pressure. The reaction mixture was filtered through Celite, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain the title compound (93.7 mg).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-33f191967e254d3f863ca6e7e74696a6
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Reaction notes

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