m-Chloroperbenzoic acid → HCID 86702135、化合物

HRID 1776191ノート

反応式

HRID 1776191 の反応式
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[CH:11]=[CH2:12])(=[O:4])=[O:3].ClC1C=CC=C(C(OO)=[O:21])C=1>C(Cl)Cl>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[CH:11]1[CH2:12][O:21]1)(=[O:4])=[O:3]

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 867021342-Ethenyl-1-(methylsulfonyl)piperidine

生成物 1

HCID 86702135HCID 86702135、化合物収率 31.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1-(methylsulfonyl)-2-vinylpiperidine (0.369 g, 2.0 mmol) in anhydrous methylene chloride (10 mL) was added purified 3-chloroperbenzoic acid (100%, 1.0 g, 6 mmol). The reaction was stirred at room temperature for 65 hours. The reaction mixture was filtered, saturated aqueous sodium sulfite added, and the biphasic solution was stirred for 5 mins. The mixture was diluted with ethyl acetate, and the organic layer successively washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride solutions, dried (anhydrous sodium sulfate), filtered, and concentrated. The crude product was purified by silica gel column chromatography (30-60% ethyl acetate in hexanes) to give a white semi-solid (0.128 g, 31%). 1H NMR (CDCl3, 300 MHz) δ 3.78-3.74 (br d, 1H, J=13.2 Hz), 3.66-3.61 (m, 1H), 3.37-3.32 (m, 1H), 3.24-3.15 (m, 1H), 2.98 (s, 3H), 2.88-2.85 (dd, 1H, J=4.8, 4.2 Hz), 2.68-2.66 (dd, 1H, J=4.8, 2.6 Hz), 1.81-1.60 (m, 6H). ESI (m/z): 205.9 (M+H).

後処理

  1. filtrationThe reaction mixture was filtered
  2. additionsaturated aqueous sodium sulfite added
  3. stirringthe biphasic solution was stirred for 5 mins
  4. additionThe mixture was diluted with ethyl acetate
  5. washthe organic layer successively washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride solutions
  6. dry with materialdried (anhydrous sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by silica gel column chromatography (30-60% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-055370e6f1be40898f8a2263275444e3
出典データセット
uspto-grants-2016_02
特許番号
US09265772B2

反応ノート

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