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Trifluoroacetic acid → Octahydro-1h-isoindol-1-one

HRID 55427
Notes
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Reaction equation

HRID 55427 reaction equation
C([N:8]1[CH2:16][CH:15]2[CH:10]([C:11](OC)(OC)[CH2:12][CH2:13][C:14]2(C2C=CC=CC=2OC)O)[CH2:9]1)C1C=CC=CC=1.C(N(CC)CC)C.FC(F)(F)C(O)=[O:40].[OH-].[Na+]>ClCCl>[C:9]1(=[O:40])[CH:10]2[CH:15]([CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:16][NH:8]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 67713918(3aRS,4RS,7aSR)-2-benzyl-7,7-dimethoxy-4-(2-methoxyphenyl)-4-perhydroisoindolol

Product 1

HCID 112047Octahydro-1h-isoindol-1-one

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 7 g of (3aRS,4RS,7aSR)-2-benzyl-7,7-dimethoxy -4-(2-methoxyphenyl)-4-perhydroisoindolol in 70 cm3 of dry dichloromethane are added 6.5 cm3 of triethylamine and 6.5 cm3 of trifluoroacetic acid. After stirring for 3 hours at room temperature, the reaction mixture, cooled to +5° C., is basified with 50 cm3 of 1N sodium hydroxide. The organic phase is separated out, washed with water, dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa). The oil obtained is crystallized in diisopropyl ether. The solid, washed with petroleum ether, is then drained and dried under reduced pressure at 40° C. 3.4 g of (3aRS,7RS,7aSR)-2-benzyl-7-hydroxy -7-(2-methoxyphenyl)-4)-perhydroisoindolone are obtained, in the form of a cream-coloured solid. M.p.=96C.

Workup

  1. temperaturethe reaction mixture, cooled to +5° C.
  2. customThe organic phase is separated out
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe oil obtained
  7. customis crystallized in diisopropyl ether
  8. washThe solid, washed with petroleum ether
  9. customdried under reduced pressure at 40° C

Sources & evidence

ORD record
ord-2b8842ef26104edf980dc39a8767d4db
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05624950

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes