Sodium borohydride → 1-(4-Bromophenyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline

HRID 397053노트

반응식

HRID 397053 반응식
[BH4-].[Na+].Cl.[Br:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13][N:12]=2)=[CH:7][CH:6]=1>CO>[Br:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13][NH:12]2)=[CH:9][CH:10]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 181724611-(4-Bromophenyl)-6-methoxy-3,4-dihydroisoquinoline hydrochloride

생성물 1

HCID 43161381-(4-Bromophenyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline수율 100%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Sodium borohydride (0.720 g, 19.0 mmol) was added in small portions to a solution of 1-(4-bromophenyl)-6-methoxy-3,4-dihydroisoquinoline, hydrochloride (3.62 g, 10.2 mmol) in MeOH (30 ml) at 0° C. The reaction mixture was stirred for 30 min, warmed to rt, and stirred at rt for 1 hr, then quenched by the dropwise addition of H2O (10 ml). Acetic acid (10 drops) was added with stirring, and the resulting mixture was basified to pH 10 with 1N NaOH and extracted with EtOAc (3×25 ml). The combined extracts were washed with 1N NaOH followed by saturated NaCl solution, dried over Na2SO4, and concentrated in vacuo to give 3.24 g (100% yield) of white solid.

후처리

  1. stirringstirred at rt for 1 hr
  2. customquenched by the dropwise addition of H2O (10 ml)
  3. additionAcetic acid (10 drops) was added
  4. stirringwith stirring
  5. extractionextracted with EtOAc (3×25 ml)
  6. washThe combined extracts were washed with 1N NaOH
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-87231351aac346acb036eadc66b2b0c2
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608203B2

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