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

HRID 415977

반응식

HRID 415977 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.[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-671ed090c526489ea143d527e9a47bc2
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088776B2

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