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

HRID 66475노트

반응식

HRID 66475 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e88779703345469098ab3abac7d57d22
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04342692

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