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

HRID 1952427

反応式

HRID 1952427 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 86654475N-Boc-3-pyrroline oxide収率 83.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e7aee4d4e5b7416a95b5334203d061ce
出典データセット
uspto-grants-2013_03
特許番号
US08404866B2

関連ノート

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