Acetic Acid → Ethyl 2-(1-cyclobutylpiperidin-4-yl)acetate

HRID 1523720ノート

反応式

HRID 1523720 の反応式
[C:1]1(=O)[CH2:4][CH2:3][CH2:2]1.C(O)(=O)C.[CH2:10]([O:12][C:13](=[O:21])[CH2:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[CH3:11].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[CH2:10]([O:12][C:13](=[O:21])[CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([CH:1]2[CH2:4][CH2:3][CH2:2]2)[CH2:17][CH2:16]1)[CH3:11]

参加物

7

反応物 5

HCID 176Acetic AcidHCID 14496CyclobutanoneHCID 516892Sodium BicarbonateHCID 2760465Ethyl 2-(piperidin-4-yl)acetateHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 86724910Ethyl 2-(1-cyclobutylpiperidin-4-yl)acetate収率 88.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A mixture of cyclobutanone (0.3 mL, 3.94 mmol) in acetic acid (0.19 mL, 3.28 mmol) was added to a stirred solution of piperidin-4-yl acetic acid ethyl ester (562 mg, 3.28 mmol, obtained in above step) in dichloromethane cooled at 0° C. Solid sodium triacetoxyborohydride (1.39 grams, 7.2 mmol) was added portion wise over a period of 15 minutes. The reaction mixture was gradually warmed to room temperature and stirred for 16 hours. The reaction mixture was cooled to 0° C. and basified with saturated sodium bicarbonate solution (pH: 7.5). The two layers were separated, the organic layer was washed with brine, dried over anhydrous sodium sulphate and the volatiles were removed under reduced pressure to obtain (1-Cyclobutyl piperidin-4-yl) acetic acid ethyl ester (652 mg).

後処理

  1. temperatureThe reaction mixture was gradually warmed to room temperature
  2. customThe two layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. customthe volatiles were removed under reduced pressure

出典と根拠

ORDレコード
ord-97a57def674c47bcb8e867a61bf32727
出典データセット
uspto-grants-2015_07
特許番号
US09079894B2

反応ノート

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