Dimethyl Sulfoxide → 7-((R)-2-formyl-6-oxo-piperidin-1-yl)-heptanoic acid methyl ester

HRID 349312ノート

反応式

HRID 349312 の反応式
CCN=C=NCCCN(C)C.CS(C)=O.[CH3:16][O:17][C:18](=[O:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[C:30](=[O:31])[CH2:29][CH2:28][CH2:27][C@@H:26]1[CH2:32][OH:33].FC(F)(F)C([O-])=O.[NH+]1C=CC=CC=1>C1C=CC=CC=1>[CH3:16][O:17][C:18](=[O:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[C:30](=[O:31])[CH2:29][CH2:28][CH2:27][C@@H:26]1[CH:32]=[O:33]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 9813011pyridine TFAHCID 690230257-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-heptanoic acid methyl ester

生成物 1

HCID 865952947-((R)-2-formyl-6-oxo-piperidin-1-yl)-heptanoic acid methyl ester

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

反応条件

温度
0 °C

実験手順

EDCI (119 mg, 0.62 mmol) and DMSO (59 μL, 0.83 mmol) were added sequentially to a solution of 7-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-heptanoic acid methyl ester (56 mg, 0.21 mmol) in benzene (2.0 mL) at rt. The mixture was cooled to 0° C. and pyridinium trifluoroacetate (44 mg, 0.23 mmol) was added. The reaction was allowed to warm to rt and then was stirred at rt for 3 h. The solution was decanted from the oily residue and the residue was washed with benzene (3×2 mL). The combined benzene phases were concentrated in vacuo to afford crude 7-((R)-2-formyl-6-oxo-piperidin-1-yl)-heptanoic acid methyl ester that was used without further purification.

後処理

  1. temperatureto warm to rt
  2. customThe solution was decanted from the oily residue
  3. washthe residue was washed with benzene (3×2 mL)
  4. concentrationThe combined benzene phases were concentrated in vacuo

出典と根拠

ORDレコード
ord-3d07f8088dae426cb53d121eb8ea217e
出典データセット
uspto-grants-2007_02
特許番号
US07179820B2

反応ノート

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