Hydrochloric Acid → (3aRS,4RS,7aRS)-7,7-diphenyl-2-phenyl-acetyl-4-perhydroisoindolol

HRID 2400023Notes

Reaction equation

HRID 2400023 reaction equation
[BH4-].[Na+].[OH-].[Na+].[C:5]1([C:11]2([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:19]3[CH:15]([CH2:16][NH:17][CH:18]3[C:20](=[O:28])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:14](=[O:29])[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl>CO.ClCCl.O>[C:30]1([C:11]2([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:19]3[CH:15]([CH2:16][NH:17][CH:18]3[C:20](=[O:28])[CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:14]([OH:29])[CH2:13][CH2:12]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 67736934HCID 67736934, compound

Product 1

HCID 67811056(3aRS,4RS,7aRS)-7,7-diphenyl-2-phenyl-acetyl-4-perhydroisoindololYield 11.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.12 g of sodium borohydride and 0.05 cm3 of 10N sodium hydroxide in 20 cm3 of methanol is added over 10 minutes to a suspension, cooled to +5° C., of 2.0 g of (3aRS,7aRS)-7,7-diphenyl-2-phenylacetyl-4-perhydro-isoindolone in 100 cm3 of methanol. The reaction mixture is stirred for 2 hours at low temperature, followed by the addition of 0.5 cm3 of 1N hydrochloric acid and concentration to a reduced volume, at 40° C. under reduced pressure (2.7 kPa). The residue is taken up in 50 cma of water and 150 cm3 of dichloromethane. After stirring, the organic phase is dried over magnesium sulphate and concentrated to dryness. The solid is crystallized from acetonitrile, the crystals are washed with acetonitrile and diisopropyl oxide, drained and then dried. 0.24 g of (3aRS,4RS,7aRS)-7,7-diphenyl-2-phenyl-acetyl-4-perhydroisoindolol is obtained in the form of white crystals; melting point 220° C.

Workup

  1. stirringAfter stirring
  2. dry with materialthe organic phase is dried over magnesium sulphate
  3. concentrationconcentrated to dryness
  4. customThe solid is crystallized from acetonitrile
  5. washthe crystals are washed with acetonitrile and diisopropyl oxide
  6. customdried

Sources & evidence

ORD record
ord-c2fd8fe3dd704448884355a87fd650c5
Source dataset
uspto-grants-1995_09
Patent number
US05451601

Reaction notes

Loading…