HCID 69698208, compound → HCID 69698059, compound

HRID 412565Notes

Reaction equation

HRID 412565 reaction equation
C([O:8][C:9](=[O:46])[CH2:10][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)C1C=CC=CC=1>O1CCCC1.CO.[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[CH2:13][CH2:12][N:11]([CH2:10][C:9]([OH:46])=[O:8])[CH2:16][CH2:15]3)=[CH:20][CH:21]=2)[CH2:26]1)=[N:30][C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])=[O:40])([CH3:43])([CH3:44])[CH3:45]

Participants

5

Reactant 1

HCID 69698208HCID 69698208, compound

Product 1

HCID 69698059HCID 69698059, compoundYield 95.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-[2-(N,N′-Di-tert-butoxycarbonylamidino)-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl]piperidine-1-acetic acid benzyl ester (735 mg) was hydrogenated using 7.5% palladium carbon (220 mg) in a mixture of tetrahydrofuran (7 ml) and methanol (14 ml) at atmospheric pressure 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 (600 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-e1b0db981ffa429c99028293f458e5da
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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