Ethyl Acetate → Ethyl 2-(2-oxo-5-phenyl-1-piperidinyl)butanoate

HRID 7399

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HRID 7399 반응식
CC(C)([O-])C.[K+].[C:7]1([CH:13]2[CH2:18][NH:17][C:16](=[O:19])[CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH:21]([CH2:27][CH3:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(OCC)(=O)C>C1(C)C=CC=CC=1>[O:19]=[C:16]1[CH2:15][CH2:14][CH:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:18][N:17]1[CH:21]([CH2:27][CH3:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 79039Butanoic acid, 2-bromo-, ethyl esterHCID 32796944-Phenyl-delta-valerolactamHCID 23665647Potassium tert-butoxide

생성물 1

HCID 11358220Ethyl 2-(2-oxo-5-phenyl-1-piperidinyl)butanoate수율 70.4%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
70 °C

실험 절차

In a 1 l three necked flask fitted with reflux condenser, magnetic stirrer and dropping funnel under inert atmosphere, 9.8 g (87 mmoles) of potassium t-butoxide were suspended in 600 ml of dry toluene. 11.8 g (67 mmoles) of 5-phenyl-2-piperidinone 25 were added, and the mixture stirred for 30 min. 17 g (87 mmoles) of ethyl 2-bromobutanoate were added and the temperature raised to 70° C. for 5 hours. 600 ml of ethyl acetate were added, the solution was washed twice with brine, the organic phase dried over magnesium sulfate, filtered and concentrated to dryness. The residue was purified by PrepLC (1 kg SiO2, CH2Cl2/EtOH, 97.5/2.5) to give 3.7 g of pure ester 26 as a mixture of diastereomers, 70.4% yield.

후처리

  1. temperaturewith reflux condenser, magnetic stirrer
  2. washthe solution was washed twice with brine
  3. dry with materialthe organic phase dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by PrepLC (1 kg SiO2, CH2Cl2/EtOH, 97.5/2.5)

출처 및 근거

ORD 기록
ord-1eef3dbcfb0c48a58fb44f859aa4293d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087596B2

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