Water → (2S,4R)-2-bromoacetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 846920ノート

反応式

HRID 846920 の反応式
[C:1]([C@@H:4]1[CH2:8][C@@H:7]([O:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH2:6][N:5]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:15])(=[O:3])[CH3:2].C1C=C[NH+]=CC=1.[Br:33][Br-]Br.O.C(OCC)(=O)C>O1CCCC1>[Br:33][CH2:2][C:1]([C@@H:4]1[CH2:8][C@@H:7]([O:9][S:10]([CH3:13])(=[O:11])=[O:12])[CH2:6][N:5]1[C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=1)=[O:15])=[O:3]

参加物

5

反応物 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 57232963(2S,4R)-2-acetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

生成物 1

HCID 14305067(2S,4R)-2-bromoacetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine収率 99%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (2S,4R)-2-acetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2.5 g) in tetrahydrofuran (80 ml) was added pyridinium bromide perbromide (2.59 g) at 5°-10° C. After stirring at room temperature for 3 hours, the mixture was poured into water (80 ml) and ethyl acetate (160 ml). The separated organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate and brine successively dried over magnesium sulfate, and evaporated in vacuo. The oily residue was subjected to a column chromatography on silica gel (60 g) eluting with a mixture of acetone and dichloromethane (1:20 V/V) to give (2S,4R)-2-bromoacetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2.98 g).

後処理

  1. washThe separated organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate and brine
  2. dry with materialsuccessively dried over magnesium sulfate
  3. customevaporated in vacuo
  4. washeluting with a mixture of acetone and dichloromethane (1:20 V/V)

出典と根拠

ORDレコード
ord-2230f8cc16ee400e928e5ad11bddaf6e
出典データセット
uspto-grants-1992_08
特許番号
US05138064

反応ノート

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