4-[(cyclohexylamino)methyl]-3,3-diphenyldihydro-2(3H)-furanone → 1-Cyclohexyl-4-hydroxymethyl-3,3-diphenyl-2-pyrrolidinone

HRID 2285770Notes

Reaction equation

HRID 2285770 reaction equation
[CH:1]1([NH:7][CH2:8][CH:9]2[CH2:13][O:12][C:11](=[O:14])[C:10]2([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[H-].[Na+].C(CC(C)(C)C)(C)C>[CH:1]1([N:7]2[CH2:8][CH:9]([CH2:13][OH:12])[C:10]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:11]2=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 128222864-[(cyclohexylamino)methyl]-3,3-diphenyldihydro-2(3H)-furanone

Product 1

HCID 128222881-Cyclohexyl-4-hydroxymethyl-3,3-diphenyl-2-pyrrolidinoneYield 73%

Reagents, catalysts & solvents 2

HCID 24758Sodium hydrideCatalystHCID 109072,2,4-TrimethylpentaneSolvent

Procedure

To 90.0 g. (0.26 mole) of 4-cyclohexylaminomethyl-4,5-dihydro-3,3-diphenylfuran-2-(3H)one in 500 ml. of isooctane was added 1.0 g. of sodium hydride (57% in mineral oil) as a catalyst and the mixture was refluxed overnight. Upon cooling a solid precipitated and the isooctane was decanted from the solid. The solid was recrystallized from isopropyl alcohol, weighed 66.0 g. (73% yield) and melted at 148°-150° C.

Workup

  1. temperatureUpon cooling a solid
  2. customprecipitated
  3. customthe isooctane was decanted from the solid
  4. customThe solid was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-b86410519fc54adbb7bf6a8680b6e675
Source dataset
uspto-grants-1982_04
Patent number
US04324791

Reaction notes

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