Water → (3R,4S)-tert-butyl 3-azido-4-(bis(4-methoxyphenyl)(phenyl)methoxy)pyrrolidine-1-carboxylate

HRID 338940ノート

反応式

HRID 338940 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:10][C@@H:11]2[C@@H:15](OS(C)(=O)=O)[CH2:14][N:13]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:12]2)=[CH:5][CH:4]=1.[N-:42]=[N+:43]=[N-:44].[Na+].O>CS(C)=O>[N:42]([C@H:15]1[C@@H:11]([O:10][C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:12][N:13]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:14]1)=[N+:43]=[N-:44]

参加物

5

反応物 3

HCID 962WaterHCID 33557Sodium AzideHCID 86707462HCID 86707462、化合物

生成物 1

HCID 86707463(3R,4S)-tert-butyl 3-azido-4-(bis(4-methoxyphenyl)(phenyl)methoxy)pyrrolidine-1-carboxylate収率 93%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
100 °C

実験手順

To a solution of (3S,4S)-tert-butyl 3-(bis(4-methoxyphenyl)(phenyl)methoxy)-4-(methylsulfonyloxy)pyrrolidine-1-carboxylate (4.0 g, 6.85 mmol) in anhydrous DMSO (70 mL) was added sodium azide (1.78 g, 27.4 mmol). The resulting mixture was heated at 100° C. for 18 hours. The solution was cooled to ambient temperature, poured into water (150 mL) and the solid which separated was collected by filtration and washed with water and dried to afford (3R,4S)-tert-butyl 3-azido-4-(bis(4-methoxyphenyl)(phenyl)methoxy)pyrrolidine-1-carboxylate (3.37 g, 93%).

後処理

  1. temperatureThe solution was cooled to ambient temperature
  2. customthe solid which separated
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried

出典と根拠

ORDレコード
ord-c7d9cc79d46948b683c5245df446a270
出典データセット
uspto-grants-2014_11
特許番号
US08889704B2

反応ノート

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