m-Chloroperbenzoic acid → N-Boc-3-pyrroline oxide

HRID 1952427

반응식

HRID 1952427 반응식
[C:1]([N:8]1[CH2:12][CH:11]=[CH:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].ClC1C=CC=C(C(OO)=[O:21])C=1>C(Cl)Cl>[C:1]([N+:8]1([O-:21])[CH2:9][CH:10]=[CH:11][CH2:12]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 5148195tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate

생성물 1

HCID 86654475N-Boc-3-pyrroline oxide수율 83.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of N-Boc-3-pyrroline (1.69 g, 10 mmol) in CH2Cl2 (20 mL) was added m-chloroperbenzoic acid (MCPBA) (˜85%, 5.2 g) in CH2Cl2 (20 mL) dropwise, and stirring was continued at room temperature overnight. The solution was extracted with saturated aqueous NaHCO3, saturated aqueous Na2SO3 and saturated aqueous NaHCO3 successively. The organic layer was dried over Na2SO4 and filtered. The solvent was evaporated and the residue was purified by flash chromatography (20% ethyl acetate in hexane) to give the product as an oil (1.54 g, 82%): 1H NMR (300 MHz, CDCl3) δ 3.77 (dd, J=22, 13 Hz, 2H), 3.66 (m, 2H), 3.31 (dd, J=13, 3 Hz, 2H), 1.44 (s, 9H).

후처리

  1. extractionThe solution was extracted with saturated aqueous NaHCO3, saturated aqueous Na2SO3 and saturated aqueous NaHCO3 successively
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customThe solvent was evaporated
  5. customthe residue was purified by flash chromatography (20% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-e7aee4d4e5b7416a95b5334203d061ce
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404866B2

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