Ammonium formate → 5-Methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 546282Notes

Reaction equation

HRID 546282 reaction equation
C([O-])=O.[NH4+].C([N:12]1[CH2:16][CH:15]2[C:17](=[CH2:26])[C:18]3[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][C:23]=3[CH:14]2[CH2:13]1)C1C=CC=CC=1>CO.[Pd]>[CH3:25][O:24][C:21]1[CH:20]=[CH:19][C:18]2[CH:17]([CH3:26])[CH:15]3[CH2:16][NH:12][CH2:13][CH:14]3[C:23]=2[CH:22]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 672038462-Benzyl-5-methoxy-8-methylene-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Product 1

HCID 115429805-Methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrroleYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Ammonium formate (8.1 g) and palladium (10 wt. % on activated carbon, 4.0 g) were added to a solution of 2-benzyl-5-methoxy-8-methylene-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (8.1 g, 27.8 mmol) in MeOH (140 mL). The reaction mixture was stirred for 4 hours at 60° C. and then filtered through celite. The celite was washed with MeOH (200 mL) and the filtrate was concentrated to afford 5.6 g (quantitative yield) of the title compound. An aliquot of the crude product was purified by reverse-phase liquid chromatography to afford the title compound. MS calculated for C13H17NO+H: 204, observed: 204.

Workup

  1. filtrationfiltered through celite
  2. washThe celite was washed with MeOH (200 mL)
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3af06468288943e7ac47c4da322278b1
Source dataset
uspto-grants-2011_05
Patent number
US07935830B2

Reaction notes

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