Ether hydrochloride → (R)-8-hydroxy5-[2-(4,7-Dimethoxy-indan-2-ylamino)-1-hydroxy-ethyl]-1H-quinolin-2-one hydrochloride

HRID 1815100Notes

Reaction equation

HRID 1815100 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([OH:36])[CH2:21][NH:22][CH:23]2[CH2:31][C:30]3[C:25](=[C:26]([O:34][CH3:35])[CH:27]=[CH:28][C:29]=3[O:32][CH3:33])[CH2:24]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)C1C=CC=CC=1.[ClH:37].C(OCC)C>CO.[Pd]>[ClH:37].[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([OH:36])[CH2:21][NH:22][CH:23]2[CH2:31][C:30]3[C:25](=[C:26]([O:34][CH3:35])[CH:27]=[CH:28][C:29]=3[O:32][CH3:33])[CH2:24]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2

Participants

5

Reactant 2

HCID 10953452Ether hydrochlorideHCID 11386205(R)-8-Benzyloxy-5-[2-(4,7-dimethoxy-indan-2-ylamino)-1-hydroxy-ethyl]-1H-quinolin-2-one

Product 1

HCID 66823337(R)-8-hydroxy5-[2-(4,7-Dimethoxy-indan-2-ylamino)-1-hydroxy-ethyl]-1H-quinolin-2-one hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(R)-8-Benzyloxy-5-[2-(4,7-dimethoxy-indan-2-ylamino)-1-hydroxy-ethyl]-1H-quinolin-2-one (37 mg, 0.08 mmol) is dissolved in methanol (10 mL) and the compound is deprotected by adding a catalytic amount of 10% palladium on charcoal and placing the solution under an atmosphere of hydrogen. The reaction is shown to be complete by TLC after 4 hours. The catalyst is filtered off, 1M HCl/diethyl ether (1.1 equivalent) is added and the solvent is removed in vacuo. TLC (silica, dichloromethane/methanol 10:1 Rf=0.15). ES+ MS m/e 397 (MH+).

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-18d9ea74a7604832ac589ac54f7f591b
Source dataset
uspto-grants-2005_04
Patent number
US06878721B1

Reaction notes

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