Diisopropylethylamine → 3-Cyclohexyl-1-(2,6-dichloro-4-methoxy-benzyl)-pyrrolidin-2-one

HRID 1670836Notes

Reaction equation

HRID 1670836 reaction equation
Br[CH2:2][CH2:3][CH:4]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[C:5]([NH:7][CH2:8][C:9]1[C:14]([Cl:15])=[CH:13][C:12]([O:16][CH3:17])=[CH:11][C:10]=1[Cl:18])=[O:6].C(N(C(C)C)CC)(C)C>C1COCC1.C(OC(=O)C)C>[CH:19]1([CH:4]2[CH2:3][CH2:2][N:7]([CH2:8][C:9]3[C:14]([Cl:15])=[CH:13][C:12]([O:16][CH3:17])=[CH:11][C:10]=3[Cl:18])[C:5]2=[O:6])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 673563304-bromo-2-cyclohexyl-N-(2,6-dichloro-4-methoxy-benzyl)-butyramide

Product 1

HCID 576580123-Cyclohexyl-1-(2,6-dichloro-4-methoxy-benzyl)-pyrrolidin-2-oneYield 80%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Treat a solution of 4-bromo-2-cyclohexyl-N-(2,6-dichloro-4-methoxy-benzyl)-butyramide (2.0 g, 4.6 mmol) in THF (30 mL) with diisopropyl ethyl amine (1.19 g, 9.19 mmol) at 40° C. for 12 hours and at reflux for 6 hours. Cool the reaction, dilute with ethylacetate and wash with HCl (1N) and water. After drying the organic layer over sodium sulfate, filtrate and concentrate under vacuum. Purify the residue by silica gel chromatography with 1:4 ethyl acetate:hexane to afford 1.3 g (80%) of the title compound. MS (m/z): 356 (M+).

Workup

  1. temperatureat reflux for 6 hours
  2. temperatureCool
  3. customthe reaction
  4. washwash with HCl (1N) and water
  5. dry with materialAfter drying the organic layer over sodium sulfate, filtrate
  6. concentrationconcentrate under vacuum
  7. customPurify the residue by silica gel chromatography with 1:4 ethyl acetate

Sources & evidence

ORD record
ord-4a72a2cacc964d179273eefcb7f3d378
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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