Methane → 7,7-Bis(2-fluorophenyl)perhydro-4-isoindolone hydrochloride

HRID 1196244Notes

Reaction equation

HRID 1196244 reaction equation
C([N:8]1[CH2:16][CH:15]2[CH:10]([C:11]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[CH2:12][CH2:13][C:14]2=[O:17])[CH2:9]1)C1C=CC=CC=1.[ClH:32].C>CO>[ClH:32].[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:11]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])[CH:10]2[CH:15]([CH2:16][NH:8][CH2:9]2)[C:14](=[O:17])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 297MethaneHCID 313Hydrochloric AcidHCID 67915773(3aRS,7aRS)-2-benzyl-7,7-bis(2-fluorophenyl)perhydro-4-isoindolone

Product 1

HCID 679159337,7-Bis(2-fluorophenyl)perhydro-4-isoindolone hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3aRS,7aRS)-2-benzyl-7,7-bis(2-fluorophenyl)perhydro-4-isoindolone (2.34 g) in methanol (100 cc), to which N hydrochloric acid (6.2 cc) is added, is hydrogenated at atmospheric pressure in the presence of palladinized charcoal (10% palladium) (0.4 g) for 5 hours at 25° C. The reaction medium is filtered and concentrated under reduced pressure (2.7 kPa) to give (3aRS,7aRS)-7,7-bis(2-fluorophenyl)perhydro-4-isoindolone hydrochloride (2 g) in the form of a white solid.

Workup

  1. filtrationThe reaction medium is filtered
  2. concentrationconcentrated under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-3732dd7b4e044763afd73bad9a30aae6
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

Loading…