Norbornadiene → (5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one

HRID 723806ノート

反応式

HRID 723806 の反応式
[S:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18][N:19]=[N+:20]=[N-:21])[O:15][C:14]3=[O:22])=[CH:9][C:8]=2[F:23])[CH2:3][CH2:2]1.[CH:24]12CC(C=C1)C=[CH:25]2>O1CCOCC1>[S:1]1[CH2:2][CH:3]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18][N:19]4[CH:25]=[CH:24][N:21]=[N:20]4)[O:15][C:14]3=[O:22])=[CH:9][C:8]=2[F:23])[CH2:5][CH2:6]1

参加物

4

反応物 2

HCID 8473NorbornadieneHCID 11450455(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-azidomethyloxazolidin-2-one

生成物 1

HCID 11302859(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one収率 73.5%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-azidomethyloxazolidin-2-one (2 g, 5.7 mmol) was dissolved in dioxane (10 ml). Bicyclo[2.2.1]hepta-2,5-diene (3.1 ml, 28.7 mmol) was added and it was refluxed under nitrogen for 18 hours. The solvent was evaporated in vacuo and the residue subjected to chromatography on silica gel eluting with 25% ethylacetate in dichloromethane to give the title compound (1.51 g).

後処理

  1. temperatureit was refluxed under nitrogen for 18 hours
  2. customThe solvent was evaporated in vacuo

出典と根拠

ORDレコード
ord-502261ae6fe846098c7d5a4f86b798a8
出典データセット
uspto-grants-2006_11
特許番号
US07141583B2

反応ノート

読み込み中…