Potassium Acetate → (3S)-3-acetoxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

HRID 891725ノート

反応式

HRID 891725 の反応式
CS([O:5][C@@H:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[CH2:7]1)(=O)=O.[C:24]([O-])(=[O:26])[CH3:25].[K+]>CN(C)C=O>[C:24]([O:5][C@H:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[CH2:7]1)(=[O:26])[CH3:25]

参加物

4

反応物 2

HCID 517044Potassium AcetateHCID 86590872HCID 86590872、化合物

生成物 1

HCID 69544124(3S)-3-acetoxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine収率 82%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of (3R)-3-methanesulfonyloxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine (7.50 g, 21.8 mmol) (obtained as described in Reference Example 52(2)) in dimethylformamide (225 ml) was added potassium acetate (6.41 g, 65.3 mmol), and the mixture was stirred in an oil bath (80° C.) overnight. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed successively with 10% aqueous sodium chloride solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (2:1→1:2) as the eluant to afford (3S)-3-acetoxy-1-(p-nitrobenzyloxycarbonyl)pyrrolidine (5.51 g, yield 82%) as white crystals.

後処理

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe organic layer was washed successively with 10% aqueous sodium chloride solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-6b48b65dc6cd428d91903a33c8752df8
出典データセット
uspto-grants-2006_02
特許番号
US07001897B2

反応ノート

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