4-Toluenesulfonyl chloride → (1-Benzylpiperidin-3-yl)methyl 4-methylbenzenesulfonate

HRID 2371139ノート

反応式

HRID 2371139 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][OH:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>ClCCl>[CH3:33][C:23]1[CH:28]=[CH:27][C:26]([S:29]([O:15][CH2:14][CH:10]2[CH2:11][CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9]2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 10398044(1-Benzylpiperidin-3-yl)methanol

生成物 1

HCID 57656889(1-Benzylpiperidin-3-yl)methyl 4-methylbenzenesulfonate収率 80.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (1-benzylpiperidin-3-yl)methanol (820 mg) and triethylamine (0.84 mL) in dichloromethane (10 mL) was added para-toluenesulfonyl chloride (846 mg). The solution was stirred overnight at room temperature. The mixture was partitioned between dichloromethane and water. The layers were separated and the organic layer was dried over sodium sulfate and evaporated. The residue was purified by silica column chromatography, eluting with a gradient of 0 to 50% ethyl acetate in hexane to give the title compound as a colourless oil (1.15 g, 80%).

後処理

  1. customThe mixture was partitioned between dichloromethane and water
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. customevaporated
  5. customThe residue was purified by silica column chromatography
  6. washeluting with a gradient of 0 to 50% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-05c245cf1ca34feb8201bc21e8b20d0f
出典データセット
uspto-grants-2014_04
特許番号
US08710224B2

反応ノート

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