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

HRID 1173829

反応式

HRID 1173829 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b64bfa3151314357a4245bf87be67758
出典データセット
uspto-grants-2010_11
特許番号
US07834194B2

関連ノート

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