Benzaldehyde → (S)-3-Benzylideneamino-2-oxo-1-piperidineacetic acid, Ethyl ester

HRID 1941446ノート

反応式

HRID 1941446 の反応式
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:3]1=[O:14].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH:15](=[N:1][C@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:3]1=[O:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 240BenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 13556450(S)-3-Amino-2-oxo-1-piperidineacetic acid, Ethyl ester

生成物 1

HCID 86751787(S)-3-Benzylideneamino-2-oxo-1-piperidineacetic acid, Ethyl ester収率 89%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 22 (4.7586 g, 0.0200 mol) and benzaldehyde (2.1224 g, 0.0200 mol, 2.03 mL) in 50 mL CH2Cl2 at 0° under N2 was added anhydrous MgSO4 (5.0 g) and Et33N (4.05 g, 0.040 mol, 5.58 mL). The mixture was stirred from 0° to ambient temperature over 21 hrs, filtered under N2, and the solvent was evaporated. The residue was dissolved in 300 mL of diethyl ether, extracted with 50 mL portions of water (3×), brine, dried over MgSO4, filtered under N2 and evaporated to afford 5.13 g (89% yield) of product 23 as a light yellow viscous oil. The material was hydrolytically labile and was stored at 0° under a N2 atmosphere.

後処理

  1. filtrationfiltered under N2
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in 300 mL of diethyl ether
  4. extractionextracted with 50 mL portions of water (3×), brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered under N2
  7. customevaporated

出典と根拠

ORDレコード
ord-4e845ac07a8541a8881d14ee867b01f3
出典データセット
uspto-grants-1997_12
特許番号
US05703208

反応ノート

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