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

HRID 1173829

반응식

HRID 1173829 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b64bfa3151314357a4245bf87be67758
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834194B2

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