Dichloromethane → Trans-2-(3,4-dihydroxybenzyl)-5-[2-(4-hydroxyphenyl)ethyl]pyrrolidine hydrobromide

HRID 66463ノート

反応式

HRID 66463 の反応式
Cl.C[O:3][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][C:25]=1[O:26]C)[CH2:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=2)[NH:9]1.C(Cl)Cl.B(Br)(Br)[Br:32]>CO>[BrH:32].[OH:3][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][C:25]=1[OH:26])[CH2:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[NH:9]1

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 13065027trans-2-(3,4-Dimethoxybenzyl)-5-[2-(4-methoxyphenyl)ethyl]pyrrolidine hydrochloride

生成物 1

HCID 13065032Trans-2-(3,4-dihydroxybenzyl)-5-[2-(4-hydroxyphenyl)ethyl]pyrrolidine hydrobromide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
-60 °C

実験手順

A solution of 1 g. (0.003 mole) of trans-2-(3,4-dimethoxybenzyl)-5-[2-(4-methoxyphenyl)ethyl]pyrrolidine hydrochloride in 35 ml. of methylene chloride was cooled to -65° C. and treated with 2.68 g. (0.012 mole) of boron tribromide dropwise. The reaction mixture was then stirred under N2 and slowly warmed from -65° to room temperature over the course of one hour and 25 minutes. The solution was then cooled again to -60° C. and 25 ml. of methanol was cautiously added. Solvent was removed in vacuo, more methanol was added and some insoluble material was filtered off. After removal of methanol in vacuo, the residue was treated with ethyl acetate. Upon standing at room temperature, 0.8 g. of product was obtained as an off-white solid, m.p. 202°-203° C.

後処理

  1. additiontreated with 2.68 g
  2. temperatureslowly warmed from -65° to room temperature over the course of one hour and 25 minutes
  3. customSolvent was removed in vacuo, more methanol
  4. additionwas added
  5. filtrationsome insoluble material was filtered off
  6. customAfter removal of methanol in vacuo
  7. additionthe residue was treated with ethyl acetate
  8. customUpon standing at room temperature
  9. customof product was obtained as an off-white solid, m.p. 202°-203° C.

出典と根拠

ORDレコード
ord-042278269e474ccbbf50cb7a7f539f67
出典データセット
uspto-grants-1982_08
特許番号
US04342692

反応ノート

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