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

HRID 415977

反応式

HRID 415977 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.[Li+].CC([N-]C(C)C)C.Br[CH2:22][C:23]1[C:28]([Cl:29])=[CH:27][C:26]([O:30][CH3:31])=[CH:25][C:24]=1[Cl:32].[Cl-].[NH4+]>O1CCCC1>[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([CH2:22][C:23]3[C:24]([Cl:32])=[CH:25][C:26]([O:30][CH3:31])=[CH:27][C:28]=3[Cl:29])[C:8]2=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 81278N-Cyclohexyl-2-pyrrolidoneHCID 2724682Lithium diisopropylamideHCID 592994792-(Bromomethyl)-1,3-dichloro-5-methoxybenzene

生成物 1

HCID 592994141-Cyclohexyl-3-(2,6-dichloro-4-methoxy-benzyl)-pyrrolidin-2-one収率 69%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

Dissolve commercially available 1-cyclohexyl-pyrrolidin-2-one (88.2 g, 527.9 mmol) in 2500 mL tetrahydrofuran and cool to −78° C. Add 176 mL 2 M LDA and stir for ˜5 min. Add 2-bromomethyl-1,3-dichloro-5-methoxy-benzene (95 g, 351.9 mmol) and allow the reaction to warm to room temperature. Pour the mixture into saturated ammonium chloride and extract twice with dichloromethane. Dry over sodium sulfate, filter and concentrate under vacuum to obtain a tan solid. Add hexanes and stir rapidly before filtering. Wash the filter cake several times with cold hexane to obtain 86 g (69%) of a light-tan solid: MS (m/z): 356 (M+).

後処理

  1. customthe reaction
  2. temperatureto warm to room temperature
  3. extractionextract twice with dichloromethane
  4. dry with materialDry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under vacuum
  7. customto obtain a tan solid
  8. filtrationbefore filtering
  9. washWash the filter cake several times with cold hexane

出典と根拠

ORDレコード
ord-671ed090c526489ea143d527e9a47bc2
出典データセット
uspto-grants-2012_01
特許番号
US08088776B2

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