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

HRID 7399

反応式

HRID 7399 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1eef3dbcfb0c48a58fb44f859aa4293d
出典データセット
uspto-grants-2006_08
特許番号
US07087596B2

関連ノート

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