Ethyl bromoacetate → Ethyl 2-(3,3-bis(4-fluorophenyl)-2-oxopiperidin-1-yl)acetate

HRID 1667170

반응식

HRID 1667170 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH2:13][CH2:12][CH2:11][NH:10][C:9]2=[O:14])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>O1CCCC1>[F:21][C:18]1[CH:17]=[CH:16][C:15]([C:8]2([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:13][CH2:12][CH2:11][N:10]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:9]2=[O:14])=[CH:20][CH:19]=1

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 23665647Potassium tert-butoxideHCID 673576463,3-Bis(4-fluorophenyl)piperidin-2-one

생성물 1

HCID 67359841Ethyl 2-(3,3-bis(4-fluorophenyl)-2-oxopiperidin-1-yl)acetate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

To the product from Example 90B (0.43 g, 1.50 mmol) as a solution in tetrahydrofuran (20 mL) was added potassium tert-butoxide (1.0 M in tetrahydrofuran) (1.80 mL, 1.80 mmol) via syringe under nitrogen followed by the addition of ethyl 2-bromoacetate (0.18 mL, 1.65 mmol). The reaction mixture heated at 80° C. and stirred overnight. The reaction mixture was cooled to room temperature, concentrated, diluted with ethyl acetate, washed with water and brine, dried with MgSO4, filtered and concentrated. Silica gel chromatography eluting with ethyl acetate/hexane (1:4) gave the title compound. MS (DCI) m/z 374 (M+H)+.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washSilica gel chromatography eluting with ethyl acetate/hexane (1:4)

출처 및 근거

ORD 기록
ord-4495887aaf8546ff838da280f2868dde
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044069B2

연결된 노트

불러오는 중…