Water → tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

HRID 358881

反応式

HRID 358881 の反応式
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([O:16][C:17]([N:19]1[CH2:23][CH:22]=[CH:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].O>C(Cl)(Cl)Cl>[C:12]([O:16][C:17]([N:19]1[CH2:23][CH:22]2[O:9][CH:21]2[CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

参加物

5

反応物 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 5148195tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate

生成物 1

HCID 10103880tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate収率 58.8%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

2.96 g (0.012 mole) of 70% aqueous m-chloroperbenzoic acid were added to a solution of 1.69 g (0.01 mole) of 1-t-butoxycarbonyl-3-pyrroline [prepared as described in Step (a) above] in 10 ml of chloroform, whilst ice-cooling, and the mixture was stirred with ice-cooling for 8 hours and then with water-cooling for 15 hours. At the end of this time, the reaction mixture was extracted with toluene and the extract was washed, in turn, with an aqueous solution of sodium bicarbonate, a 0.1N aqueous solution of sodium thiosulfate and water. It was then dried over anhydrous sodium sulfate, and the solvent was removed by evaporation under reduced pressure. The residue was subjected to silica gel column chromatography eluted with a 1:5 by volume mixture of ethyl acetate and toluene, to afford 1.09 g of 1-t-butoxycarbonyl-3,4-epoxypyrrolidine as a colorless oily substance.

後処理

  1. temperaturecooling
  2. temperaturecooling for 8 hours
  3. extractionAt the end of this time, the reaction mixture was extracted with toluene
  4. washthe extract was washed, in turn, with an aqueous solution of sodium bicarbonate
  5. dry with materialIt was then dried over anhydrous sodium sulfate
  6. customthe solvent was removed by evaporation under reduced pressure
  7. washeluted with a 1:5 by volume mixture of ethyl acetate and toluene

出典と根拠

ORDレコード
ord-3b5843a477ee452f954ed9e0b498034d
出典データセット
uspto-grants-1991_03
特許番号
US04997943

関連ノート

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