Diisopropylamine → Methyl 4-(2-benzyloxyphenyl)-2-(cyclohexylcarbonyl)butyrate

HRID 1533258Notes

Reaction equation

HRID 1533258 reaction equation
C([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH:42]1([C:48](Cl)=[O:49])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1>O1CCCC1.CCCCCC>[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][CH2:36][CH:37]([C:48]([CH:42]1[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1)=[O:49])[C:38]([O:40][CH3:41])=[O:39])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 2724682Lithium diisopropylamideHCID 22012370Methyl 4-(2-benzyloxyphenyl)butyrateHCID 178418339Butyllithium

Product 1

HCID 22012461Methyl 4-(2-benzyloxyphenyl)-2-(cyclohexylcarbonyl)butyrateYield 48.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a dry ice-acetone bath cooled solution of lithium diisopropylamide, prepared from diisopropylamine (222 mg) and 1.61M hexane solution of n-butyllithium (1.24 ml) in tetrahydrofuran (5.6 ml), was added methyl 4-(2-benzyloxyphenyl)butyrate (284 mg) and the mixture was stirred for 30 minutes at the same temperature. Cyclohexanecarbonyl chloride (176 mg) was added. After being stirred for 30 minutes the reaction mixture was quenched by 1N hydrochloric acid solution and the organic layer was separated. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with aqueous sodium bicarbonate solution and brine, and dried. The solvent was evaporated in vacuo and the residue was purified by preparative thin layer chromatography [silica gel, ether - n-hexane (1:4)] to afford methyl 4-(2-benzyloxyphenyl)-2-(cyclohexylcarbonyl)butyrate (190 mg).

Workup

  1. stirringAfter being stirred for 30 minutes the reaction mixture
  2. customwas quenched by 1N hydrochloric acid solution
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layer was washed with aqueous sodium bicarbonate solution and brine
  6. customdried
  7. customThe solvent was evaporated in vacuo
  8. customthe residue was purified by preparative thin layer chromatography [silica gel, ether - n-hexane (1:4)]

Sources & evidence

ORD record
ord-364b144ba91943ada6c5208408dac14c
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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