Methanol → 2-(3',4'-Dihydroxybenzyl)-5-(2-phenylethyl) pyrrolidine hydrobromide

HRID 256202ノート

反応式

HRID 256202 の反応式
C[O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[O:23]C)[CH2:6][CH:7]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:8]1.B(Br)(Br)[Br:26].CO>C(Cl)Cl>[BrH:26].[OH:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[OH:23])[CH2:6][CH:7]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:8]1

参加物

5

反応物 3

HCID 887MethanolHCID 25134Boron tribromideHCID 130650362-(3'4'-Dimethoxybenzyl)-5-(2-phenylethyl)pyrrolidine

生成物 1

HCID 130650372-(3',4'-Dihydroxybenzyl)-5-(2-phenylethyl) pyrrolidine hydrobromide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a cold (-70° C.) solution of 15.1 g (0.057 mole) of 2-(3'4'-dimethoxybenzyl)-5-(2-phenylethyl)pyrrolidine in 1 L of methylene chloride was added dropwise 55.1 g (0.22 mole) of boron tribromide. After the addition the reaction mixture was gradually warmed up to room temperature over a period of 2 h. 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 dark residue was boiled in ethyl acetate and decanted, then triturated with ethyl acetate and left overnight to give a solid. This was recrystallized twice from acetonitrile to give 6 g. m.p. 149°-151° C.

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. customThis was recrystallized twice from acetonitrile
  10. customto give 6 g

出典と根拠

ORDレコード
ord-2169a1109d5c4e08a3ade7d3c02f1ef8
出典データセット
uspto-grants-1987_10
特許番号
US04701461

反応ノート

読み込み中…