Methyl 2-{4-[1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate → Methyl 2-{4-[1-(tert-butoxycarbonyl)piperidin-4-yl]benzyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate

HRID 1622307Notes

Reaction equation

HRID 1622307 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:34]=[CH:33][C:17]([CH2:18][N:19]3[CH2:28][CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:29]([O:31][CH3:32])=[O:30])[CH:25]=4)[CH2:20]3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[CH:16][C:17]([CH2:18][N:19]3[CH2:28][CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:29]([O:31][CH3:32])=[O:30])[CH:25]=4)[CH2:20]3)=[CH:33][CH:34]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67980088Methyl 2-{4-[1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate

Product 1

HCID 67980341Methyl 2-{4-[1-(tert-butoxycarbonyl)piperidin-4-yl]benzyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylateYield 87.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl 2-{4-[1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (228 mg, 0.493 mmol) in MeOH (5.0 mL) was degassed thoroughly and palladium on carbon (5% Pd/C, 15.6 mg, 0.0025 mmol) was added. The mixture was stirred at rt under an atmosphere of hydrogen gas for 2 h. The reaction mixture was filtered through a pad of Celite, and the filtrate was concentrated to give methyl 2-{4-[1-(tert-butoxycarbonyl)piperidin-4-yl]benzyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (200 mg, 87%) which was used without purification. LC-MS: (FA) ES+ 465.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a32ed692e293451d819af16a23d59fdc
Source dataset
uspto-grants-2014_07
Patent number
US08778931B2

Reaction notes

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