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

HRID 270042
ノート
印刷プレビュー

反応式

HRID 270042 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8c18a58d889846d2979008f65b8a549d
出典データセット
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07449475B2

反応ノート

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