Triethylamine → 1-[4-(Tributylstannyl)-3,6-dihydropyridin-1(2H)-yl]ethan-1-one

HRID 2166496ノート

反応式

HRID 2166496 の反応式
[C:1]([N:4]1[CH2:9][CH2:8][C:7](O)([Sn:10]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH2:13][CH3:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O>C(Cl)Cl>[C:1]([N:4]1[CH2:5][CH:6]=[C:7]([Sn:10]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:15][CH2:16][CH2:17][CH3:18])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 156368991-Acetyl-4-hydroxy-4-tributylstannyl-piperidine2 回

生成物 1

HCID 156368961-[4-(Tributylstannyl)-3,6-dihydropyridin-1(2H)-yl]ethan-1-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

1-Acetyl-4-hydroxy-4-tributylstannyl-piperidine, 20 (16.4 g, 38 mmol) and triethylamine (15.0 ml, 108 mmol) were dissolved in methylene chloride (250 ml) and the solution cooled to 0° C. Methanesulfonylchloride (6.0 ml, 50 mmol) in methylene chloride (50 ml) was added dropwise to the cooled solution and the mixture was allowed to warm to room temperature and stir for 60 hours. The reaction solution was washed with NaCl solution, dried (MgSO4), filtered, and evaporated to give a red oil which was purified by flash column chromatography on silica gel, eluting with 3% ethanol in CH2Cl2. After combining the appropriate fractions and evaporating the solvent, the title compound, 21, was obtained (7.5 g).

後処理

  1. temperatureto warm to room temperature
  2. washThe reaction solution was washed with NaCl solution
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give a red oil which
  7. customwas purified by flash column chromatography on silica gel
  8. washeluting with 3% ethanol in CH2Cl2
  9. customevaporating the solvent

出典と根拠

ORDレコード
ord-e7279b2515a4451cac7ec3db49515000
出典データセット
uspto-grants-1990_07
特許番号
US04945160

反応ノート

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