Ammonium Chloride → (2S,4S)-1-allyloxycarbonyl-4-azido-2-hydroxymethylpyrrolidine

HRID 1650277ノート

反応式

HRID 1650277 の反応式
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10](OS(C)(=O)=O)[CH2:9][C@H:8]1[CH2:17][OH:18])=[O:6])[CH:2]=[CH2:3].[Cl-].[NH4+].[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C)C=O.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([N:21]=[N+:22]=[N-:23])[CH2:9][C@H:8]1[CH2:17][OH:18])=[O:6])[CH:2]=[CH2:3]

参加物

7

反応物 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 18639172(2S,4R)-1-allyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol

生成物 1

HCID 57320993(2S,4S)-1-allyloxycarbonyl-4-azido-2-hydroxymethylpyrrolidine

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
75 °C

実験手順

To a solution of (2S,4R)-1-allyloxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxypyrrolidine (20.0 g) in N,N-dimethylformamide (200 ml) were added ammonium chloride (5.74 g) and sodium azide (6.98 g). The resulting mixture was heated at 75° C for 8 hours. After cooling, the mixture was diluted with ethyl acetate (1 l) and aqueous sodium hydrogen carbonate (1 l). The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated in vacuo to give (2S,4S)-1-allyloxycarbonyl-4-azido-2-hydroxymethylpyrrolidine.

後処理

  1. temperatureAfter cooling
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

出典と根拠

ORDレコード
ord-6893a28236a8426fa0b27dcdd21a0f3a
出典データセット
uspto-grants-1990_05
特許番号
US04923857

反応ノート

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