Methanol → 2-(3',4'-Dihydroxybenzyl)-5-[2-(4-chlorophenyl)ethyl]pyrrolidine hydrobromide

HRID 1589377ノート

反応式

HRID 1589377 の反応式
C[O:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][C:23]=1[O:24]C)[CH2:6][CH:7]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[NH:8]1.B(Br)(Br)[Br:27].CO>C(Cl)Cl>[BrH:27].[OH:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][C:23]=1[OH:24])[CH2:6][CH:7]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[NH:8]1

参加物

5

反応物 3

HCID 887MethanolHCID 25134Boron tribromideHCID 201642172-(3',4'-Dimethoxybenzyl)-5-[2-(4-chlorophenyl)ethyl]pyrrolidine

生成物 1

HCID 201642162-(3',4'-Dihydroxybenzyl)-5-[2-(4-chlorophenyl)ethyl]pyrrolidine hydrobromide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a cold (-70° C.) solution of 24.2 g (0.67 mole) of 2-(3',4'-dimethoxybenzyl)-5-[2-(4-chlorophenyl)ethyl]pyrrolidine in 600 cc of methylene chloride was added dropwise 46.5 g (0.186 mole) of boron tribromide. After the addition the reaction mixture was gradually warmed to room temperature over a period of 2 hours. The mixture was cooled again to -70° C. and 300 ml of methanol was carefully added. Solvent was removed in vacuo. An additional 100 ml of methanol was added and removed in vacuo. The gummy residue was boiled in ethyl acetate and decanted, then triturated with ethyl acetate and left in the refrigerator overnight to give a solid. After recrystallization from a minimum amount of methanol there was obtained 7.05 g.

後処理

  1. additionAfter the addition the reaction mixture
  2. temperatureThe mixture was cooled again to -70° C.
  3. customSolvent was removed in vacuo
  4. additionAn additional 100 ml of methanol was added
  5. customremoved in vacuo
  6. customdecanted
  7. customtriturated with ethyl acetate
  8. customto give a solid
  9. customAfter recrystallization from a minimum amount of methanol
  10. customthere was obtained 7.05 g

出典と根拠

ORDレコード
ord-3e808f4176d34499a02a7375f4cb436c
出典データセット
uspto-grants-1986_02
特許番号
US04569941

反応ノート

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