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

HRID 256197노트

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HRID 256197 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
60 °C

실험 절차

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 31 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.

후처리

  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.

출처 및 근거

ORD 기록
ord-663097130f4a4798922fa184fac3f9f6
출처 데이터셋
uspto-grants-1987_10
특허 번호
US04701461

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