Methyl chloroformate → Dimethyl 2-(4-fluorobenzyl)piperidine-1,4-dicarboxylate

HRID 1963268ノート

反応式

HRID 1963268 の反応式
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][CH:7]2[CH2:12][CH:11]([C:13]([O:15][CH3:16])=[O:14])[CH2:10][CH2:9][NH:8]2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:28](Cl)(=[O:31])[O:29][CH3:30]>C(Cl)Cl.C(Cl)(=O)OC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:12][CH:11]([C:13]([O:15][CH3:16])=[O:14])[CH2:10][CH2:9][N:8]2[C:28]([O:29][CH3:30])=[O:31])=[CH:17][CH:18]=1

参加物

6

反応物 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731633HCID 66731633、化合物

生成物 1

HCID 66735290Dimethyl 2-(4-fluorobenzyl)piperidine-1,4-dicarboxylate収率 95%

試薬・触媒・溶媒 2

HCID 6586Methyl chloroformate触媒HCID 6344Dichloromethane溶媒

実験手順

Methyl 2-(4-fluorobenzyl)piperidine-4-carboxylate (4.981 g, 19.82 mmol) was dissolved in DCM (150 mL) and DIPEA (4.14 mL, 23.79 mmol), then methyl carbonochloridate (1.873 mL, 23.79 mmol) was added. The solution was stirred at room temperature for 50 min. More methyl carbonochloridate (a few drops) were added and the reaction continued at room temperature for 1 h. The reaction mixture was washed with 0.1 M HCl and satd NaHCO3. The organic phase was passed through a phase separator and evaporated to yield dimethyl 2-(4-fluorobenzyl)piperidine-1,4-dicarboxylate (5.82 g, 95%) as a yellow oil. MS m/z 310 (M+H)+

後処理

  1. waitthe reaction continued at room temperature for 1 h
  2. washThe reaction mixture was washed with 0.1 M HCl
  3. customevaporated

出典と根拠

ORDレコード
ord-9e4c0eaf21e74859b736c37e41ad6eb0
出典データセット
uspto-grants-2013_04
特許番号
US08415378B2

反応ノート

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