m-Chloroperbenzoic acid → HCID 86702135, 화합물

HRID 1776191노트

반응식

HRID 1776191 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 86702135HCID 86702135, 화합물수율 31.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-055370e6f1be40898f8a2263275444e3
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265772B2

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