Dimethyl Sulfoxide → 7-(2-Formyl-6-oxo-piperidin-1-yl)-hept-5-ynoic acid methyl ester

HRID 352404ノート

反応式

HRID 352404 の反応式
CS(C)=O.[CH3:5][O:6][C:7](=[O:23])[CH2:8][CH2:9][CH2:10][C:11]#[C:12][CH2:13][N:14]1[C:19](=[O:20])[CH2:18][CH2:17][CH2:16][CH:15]1[CH2:21][OH:22].FC(F)(F)C([O-])=O.[NH+]1C=CC=CC=1>C1C=CC=CC=1>[CH3:5][O:6][C:7](=[O:23])[CH2:8][CH2:9][CH2:10][C:11]#[C:12][CH2:13][N:14]1[C:19](=[O:20])[CH2:18][CH2:17][CH2:16][CH:15]1[CH:21]=[O:22]

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 9813011pyridine TFAHCID 690203407-(2-Hydroxymethyl-6-oxo-piperidin-1-yl)-hept-5-ynoic acid methyl ester

生成物 1

HCID 860125007-(2-Formyl-6-oxo-piperidin-1-yl)-hept-5-ynoic 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

1-(3-(Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 530 mg, 2.76 mmol) and DMSO (0.26 mL, 3.68 mmol) were added sequentially to a solution of 7-(2-hydroxymethyl-6-oxo-piperidin-1-yl)-hept-5-ynoic acid methyl ester (246 mg, 0.92 mmol) in benzene (7.0 mL) at rt. The mixture was cooled to 0° C. and pyridinium trifluoroacetate (196 mg, 1.01 mmol) was added. The reaction was allowed to warm to rt and then was stirred at rt for 2.5 h. The solution was decanted from the oily residue and the residue was washed with benzene (3×5 mL). The combined benzene phases were concentrated in vacuo to afford crude 7-(2-formyl-6-oxo-piperidin-1-yl)-hept-5-ynoic 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 (3×5 mL)
  4. concentrationThe combined benzene phases were concentrated in vacuo

出典と根拠

ORDレコード
ord-f0eea8d402f548e19a0d32a705e989b7
出典データセット
uspto-grants-2004_06
特許番号
US06747037B1

反応ノート

読み込み中…