Sodium Azide → (3aRS,4RS,6SR,7aSR)-6-azidomethyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]perhydroisoindol-4-ol

HRID 1599156ノート

反応式

HRID 1599156 の反応式
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1([OH:44])[CH2:21][CH:20]([CH2:22]S(C2C=CC(C)=CC=2)(=O)=O)[CH2:19][CH:18]2[CH:14]1[CH2:15][N:16]([C:33](=[O:43])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[O:41][CH3:42])[CH2:17]2>CN(C)C=O.O>[N:1]([CH2:22][CH:20]1[CH2:19][CH:18]2[CH:14]([CH2:15][N:16]([C:33](=[O:43])[CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[O:41][CH3:42])[CH2:17]2)[C:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH3:5])([OH:44])[CH2:21]1)=[N+:2]=[N-:3]

参加物

5

反応物 2

HCID 33557Sodium AzideHCID 86752423(3aRS,4RS,6SR,7aSR)-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-6-tosylmethylperhydroisoindol-4-ol

生成物 1

HCID 86752422(3aRS,4RS,6SR,7aSR)-6-azidomethyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]perhydroisoindol-4-ol収率 98.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

0.35 g of sodium azide is added to a solution of 2.03 g of (3aRS,4RS,6SR,7aSR)-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-6-tosylmethylperhydroisoindol-4-ol in 10 cm3 of dimethylformamide. The reaction mixture is heated at 50° C. for 8 hours and stirred at 20° C. for 48 hours and then diluted with 150 cm3 of water and subjected to extraction twice with 40 cm3 of ethyl acetate. The organic phase is washed with 50 cm3 of water, dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa). 1.6 g of (3aRS,4RS,6SR,7aSR)-6-azidomethyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]perhydroisoindol-4-ol are obtained in the form of a thick white foam.

後処理

  1. extractionsubjected to extraction twice with 40 cm3 of ethyl acetate
  2. washThe organic phase is washed with 50 cm3 of water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

出典と根拠

ORDレコード
ord-c1a950fb6ba94e648caed20f953e4756
出典データセット
uspto-grants-1998_04
特許番号
US05739351

反応ノート

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