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alpha-Bromo-o-fluorotoluene → Ethyl 1-benzyl-4-(2-fluorobenzyl)piperidine-4-carboxylate

HRID 270042
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HRID 270042 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[F:29][C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32]Br>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:32][C:31]2[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=2[F:29])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 67968alpha-Bromo-o-fluorotolueneHCID 90423Ethyl 1-benzylpiperidine-4-carboxylateHCID 2733832Lithium hexamethyldisilazane

생성물 1

HCID 59833634Ethyl 1-benzyl-4-(2-fluorobenzyl)piperidine-4-carboxylate수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

Ethyl 1-benzylpiperidine-4-carboxylate (2.47 g, 10 mmol) was dissolved in tetrahydrofuran (20 mL) and cooled to −78° C. Lithium bis(trimethylsilyl)amide (11 mL, 1.0 M in tetrahydrofuran) was added slowly, and stirred for 30 minutes. 2-fluoro-benzylbromide (1.34 mL, 11 mmol) in 5 mL tetrahydrofuran was added slowly. The resulting solution was allowed to reach room temperature and stirred over night. The reaction was quenched with ammonium chloride (aq, sat) and partitioned between water and ethyl acetate. The organic layer was washed with brine and dried over magnesium sulphate, filtrated and concentrated. The crude material was purified on silica (heptane/ethyl acetate), to give 2.7 g (77%) the subtitle compound as a colourless oil.

후처리

  1. customto reach room temperature
  2. stirringstirred over night
  3. customThe reaction was quenched with ammonium chloride (aq, sat)
  4. custompartitioned between water and ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltrated
  8. concentrationconcentrated
  9. customThe crude material was purified on silica (heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-8c18a58d889846d2979008f65b8a549d
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07449475B2

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