4-[2-(N,N'-Di-tert-butoxycarbonylamidino)-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl]piperidine-1-carboxylic acid benzyl ester → N,N'-ditert-butoxycarbonyl-7-(piperidin-4-ylmethoxy)-1,2,3,4-tetrahydroisoquinoline-2-carboxamidine

HRID 412559Notes

Reaction equation

HRID 412559 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](=[N:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26]3)=[CH:21][CH:20]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>O1CCCC1.C(O)C.[C].[Pd]>[C:42]([O:41][C:39]([NH:38][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[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]3)=[CH:20][CH:21]=2)[CH2:26]1)=[N:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[O:40])([CH3:43])([CH3:44])[CH3:45]

Participants

5

Reactant 1

HCID 600641014-[2-(N,N'-Di-tert-butoxycarbonylamidino)-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl]piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 60064218N,N'-ditert-butoxycarbonyl-7-(piperidin-4-ylmethoxy)-1,2,3,4-tetrahydroisoquinoline-2-carboxamidineYield 207.7%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-[2-(N,N′-Di-tert-butoxycarbonylamidino)-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl]piperidine-1-carboxylic acid benzyl ester (500 mg) was hydrogenated using 7.5% palladium carbon (150 mg) in a mixture of tetrahydrofuran (5 ml) and ethanol (100 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-3f6b6b55cdc1415784204056d37e2103
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

Loading…