Ammonium formate → {6-Hydroxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl}-phenylmethanone

HRID 397075Notes

Reaction equation

HRID 397075 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:21][CH:20]=1)[N:14]([C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:34])[CH2:13][CH2:12]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]([C:19]1[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32]3)=[CH:23][CH:24]=1)[N:14]([C:33]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:34])[CH2:13][CH2:12]2

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 12085948{6-Benzyloxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-3,4-dihydro-1H-isoquinolin-2-yl}phenylmethanone

Product 1

HCID 12085942{6-Hydroxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl}-phenylmethanoneYield 79.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of {6-benzyloxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-3,4-dihydro-1H-isoquinolin-2-yl}phenylmethanone (0.043 g, 0.08 mmol), ammonium formate (0.127 g, 2.01 mmol), and 20% Pd(OH)2/C (0.025 g) in MeOH (10 ml) was refluxed under N2 for 1 hr, then filtered through Celite. The filtrate was evaporated in vacuo to a white residue that was dissolved in CH2Cl2 (10 ml) and washed with 1M NaOH (5 ml). The aqueous layer was extracted with CH2Cl2 (3×10 ml) and all of the combined organic solutions were dried over MgSO4 and concentrated in vacuo to give 0.028 g (78% yield) of colorless residue.

Workup

  1. temperaturewas refluxed under N2 for 1 hr
  2. filtrationfiltered through Celite
  3. customThe filtrate was evaporated in vacuo to a white residue that
  4. dissolutionwas dissolved in CH2Cl2 (10 ml)
  5. washwashed with 1M NaOH (5 ml)
  6. extractionThe aqueous layer was extracted with CH2Cl2 (3×10 ml)
  7. dry with materialall of the combined organic solutions were dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a49f1f35dd14e669579c560051f915d
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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