Diisopropylethylamine → 1-[1-(4-Chloro-phenyl)-cyclobutanecarbonyl]-piperidin-3-ylmethyl alcohol

HRID 586380ノート

反応式

HRID 586380 の反応式
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][OH:8])[CH2:2]1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:20](O)=[O:21])[CH2:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1.C(N(C(C)C)CC)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>ClCCl>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2([C:20]([N:1]3[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][OH:8])[CH2:2]3)=[O:21])[CH2:19][CH2:18][CH2:17]2)=[CH:14][CH:15]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 107308Piperidin-3-ylmethanolHCID 6027611-(p-Chlorophenyl)cyclobutanecarboxylic acidHCID 2733179PyBroP

生成物 1

HCID 219020351-[1-(4-Chloro-phenyl)-cyclobutanecarbonyl]-piperidin-3-ylmethyl alcohol収率 43.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 3-piperidinemethanol (5.0 g, 43.4 mmol), 1-(4-chlorophenyl)-1-cyclobutanecarboxylic acid (9.14 g, 43.4 mmol), and diisopropylethylamine (11.22 g, 86.8 mmol) in dichloromethane (100 mL) at 0° C. was added PyBroP® (22.26 g, 47.8 mmol). The reaction was stirred at 0° C. for 1 h and then at room temperature for 4 h. The reaction mixture was washed successively with water, 1 N HCl, water, sat. sodium bicarbonate solution, and water (100 mL each). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated by rotary evaporation. The residue was purified by chromatography on silica gel, eluting with dichloromethane/methanol (96:4) to give 5.8 g of the amide 1 as a thick gum.

後処理

  1. waitat room temperature for 4 h
  2. washThe reaction mixture was washed successively with water, 1 N HCl, water, sat. sodium bicarbonate solution, and water (100 mL each)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customThe residue was purified by chromatography on silica gel
  7. washeluting with dichloromethane/methanol (96:4)

出典と根拠

ORDレコード
ord-0a89286097084166ad907101fbf5a093
出典データセット
uspto-grants-2005_08
特許番号
US06936614B2

反応ノート

読み込み中…