N-Cyclohexyl-2-pyrrolidone → 3-Benzo[b]thiophen-2-ylmethyl-1-cyclohexyl-pyrrolidin-2-one

HRID 1173829

Reaction equation

HRID 1173829 reaction equation
[CH:1]1([N:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([N-]C(C)C)(C)C.[Li+].Br[CH2:22][C:23]1[S:27][C:26]2[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=2[CH:24]=1>C1COCC1>[S:27]1[C:23]([CH2:22][CH:9]2[CH2:10][CH2:11][N:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[C:8]2=[O:12])=[CH:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]1=2

Participants

5

Reactant 3

HCID 81278N-Cyclohexyl-2-pyrrolidoneHCID 2724682Lithium diisopropylamideHCID 136426052-(Bromomethyl)benzo[b]thiophene

Product 1

HCID 116453263-Benzo[b]thiophen-2-ylmethyl-1-cyclohexyl-pyrrolidin-2-oneYield 71.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Place 1-cyclohexyl-pyrrolidin-2-one (500 mg) in THF (30 mL) and cool to −78° C. Slowly add lithium diisopropylamide (LDA) (2M, 1.5 eq) and stir for 15 minutes. Add 2-bromomethyl-benzo[b]thiophene [J. Med. Chem. (1992) 1176-1183] (815 mg, 3.59 mmol) and stir for 3 hours. Quench with ammonium chloride and extract with dichloromethane. Dry over sodium sulfate, filter, and concentrate. Purify by silica gel (20-50% ethyl acetate in hexanes) to give 670 mg, 71% of the title compound as a white powder. MS (APCI-pos mode) m/z (rel intensity) 314 (100).

Workup

  1. customQuench with ammonium chloride
  2. extractionextract with dichloromethane
  3. dry with materialDry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify by silica gel (20-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b64bfa3151314357a4245bf87be67758
Source dataset
uspto-grants-2010_11
Patent number
US07834194B2

Linked notes

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