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

HRID 1523720노트

반응식

HRID 1523720 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-97a57def674c47bcb8e867a61bf32727
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079894B2

반응 노트

불러오는 중…