4-(2-tert-Butoxycarbonyl-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)piperidine-1-carboxylic acid benzyl ester → 7-(Piperidin-4-ylmethoxy)-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester

HRID 412572Notes

Reaction equation

HRID 412572 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][O:18][C:19]2[CH:28]=[C:27]3[C:22]([CH2:23][CH2:24][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:26]3)=[CH:21][CH:20]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>O1CCCC1.CO.[C].[Pd]>[C:32]([O:31][C:29]([N:25]1[CH2:24][CH2:23][C:22]2[C:27](=[CH:28][C:19]([O:18][CH2:17][CH:14]3[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]3)=[CH:20][CH:21]=2)[CH2:26]1)=[O:30])([CH3:35])([CH3:33])[CH3:34]

Participants

5

Reactant 1

HCID 112486364-(2-tert-Butoxycarbonyl-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 112794437-(Piperidin-4-ylmethoxy)-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl esterYield 87%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(2-tert-Butoxycarbonyl-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl)-piperidine-1-carboxylic acid benzyl ester (1.3 g) was hydrogenated using 7.5% palladium carbon (300 mg) in a mixture of tetrahydrofuran (10 ml) and methanol (20 ml) at 3 atm over 3 hours. After completion of the reaction, the reaction mixture was filtered through celite and the solvent was evaporated. The residue was dried under reduced pressure to give the title compound (815 mg).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through celite
  3. customthe solvent was evaporated
  4. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-338a97f378154911b7b0c6df1d456080
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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