Triethylamine → Ethyl 1-(2,2-dimethylpropanoyl)piperidine-4-carboxylate

HRID 12396

反応式

HRID 12396 の反応式
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:19][C:20]([CH3:25])([CH3:24])[C:21](Cl)=[O:22]>ClCCl>[C:21]([N:1]1[CH2:2][CH2:3][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:10][CH2:11]1)(=[O:22])[C:20]([CH3:25])([CH3:24])[CH3:19]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 70770Ethyl 4-piperidinecarboxylate

生成物 1

HCID 1164515Ethyl 1-(2,2-dimethylpropanoyl)piperidine-4-carboxylate収率 94%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Ethyl isonipecotate (20 mL, 130 mmol) was dissolved in 130 mL of dichloromethane and cooled to 0° C. and triethyl amine (19.9 mL, 143 mmol) was added. Trimethylacetyl chloride (16.8 mL, 136 mmol) was added dropwise and the reaction was allowed to warm to rt and stirred for 16 h. The reaction mixture was washed with hydrochloric acid solution (1.0 M, aq), sodium bicarbonate (sat., aq.) and sodium chloride (sat., aq.). The organic layer dried over magnesium sulfate, filtered and the solvent removed to provide 29.5 g (94%) of 20a as a pale orange liquid. LC-MS m/z 242 [M+H]+.

後処理

  1. temperatureto warm to rt
  2. washThe reaction mixture was washed with hydrochloric acid solution (1.0 M, aq), sodium bicarbonate (sat., aq.) and sodium chloride (sat., aq.)
  3. dry with materialThe organic layer dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed

出典と根拠

ORDレコード
ord-54295f7da89143368c391cc8da153b10
出典データセット
uspto-grants-2010_06
特許番号
US07728008B2

関連ノート

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