p-Toluenesulfonic acid → (S)alpha-[(2S)(6-bromo-hexahydro-3,5-methano-2H-cyclopenta[b]furan-2-yl)-oxy]-3-phenoxy-benzene-acetonitrile

HRID 256231

反応式

HRID 256231 の反応式
[Br:1][CH:2]1[CH:6]2[O:7][CH:8]([OH:11])[CH:9]3[CH2:10][CH:3]1[CH2:4][CH:5]23.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15](S(O)(=O)=O)=[CH:14][CH:13]=1.C[N:24]([CH3:27])C=O>C(Cl)Cl>[Br:1][CH:2]1[CH:6]2[O:7][C@H:8]([O:11][C@@H:22]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:7][C:6]4[CH:2]=[CH:3][CH:10]=[CH:9][CH:5]=4)[CH:13]=3)[C:27]#[N:24])[CH:9]3[CH2:10][CH:3]1[CH2:4][CH:5]23

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 6228Dimethylformamide2 回HCID 212840296-bromo-hexahydro-3,5-methano-2H-cyclopenta[b]furan-2-ol

生成物 1

HCID 70372766(S)alpha-[(2S)(6-bromo-hexahydro-3,5-methano-2H-cyclopenta[b]furan-2-yl)-oxy]-3-phenoxy-benzene-acetonitrile

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 2.19 g of the product of Step B in 50 ml of methylene chloride was added to a refluxing mixture of 2.93 g of (R,S)α-cyano-3-phenoxy-benzyl alcohol, 100 ml of methylene chloride and 300 mg of p-toluene sulfonic acid and the mixture was refluxed for another 15 minutes and then returned to room temperature. The mixture was washed with water, dried, vacuum filtered and evaporated to dryness under reduced pressure. The 4.34 g of the (R,S)α-[(2S)(6-bromo-hexahydro-3,5-methano-2H-cyclopenta[b]furan-2-yl)-oxy]-3-phenoxy-benzene acetonitrile were chromatographed over silica gel and eluted with a 9-1 hexane-ethyl acetate mixture to obtain the (S)α-isomer melting at 65° C. and having a specific rotation of [α]D20 =+110° (c=0.5% in dimethylformamide) and the (R)α-isomer with a specific rotation of [α]D20 =+108.5° (c=0.4% in dimethylformamide).

後処理

  1. temperaturethe mixture was refluxed for another 15 minutes
  2. customreturned to room temperature
  3. washThe mixture was washed with water
  4. customdried
  5. filtrationvacuum filtered
  6. customevaporated to dryness under reduced pressure
  7. customThe 4.34 g of the (R,S)α-[(2S)(6-bromo-hexahydro-3,5-methano-2H-cyclopenta[b]furan-2-yl)-oxy]-3-phenoxy-benzene acetonitrile were chromatographed over silica gel
  8. washeluted with a 9-1 hexane-ethyl acetate mixture
  9. customto obtain the (S)α-isomer melting at 65° C.

出典と根拠

ORDレコード
ord-89580c9318d1433dae774e68bc085dd8
出典データセット
uspto-grants-1987_10
特許番号
US04701542

関連ノート

読み込み中…