Sodium borohydride → 4,4-Dimethyl-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

HRID 445285노트

반응식

HRID 445285 반응식
[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[N:4][CH2:3]1.[BH4-].[Na+]>CO>[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:14][CH:13]=2)[NH:4][CH2:3]1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 595364234,4-Dimethyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline

생성물 1

HCID 595363404,4-Dimethyl-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A 50-mL round-bottomed flask was charged with 4,4-dimethyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline (2.52 g, 8.3 mmol) and dry MeOH (10 mL). After cooling down to 0° C. sodium borohydride (943 mg, 24.9 mmol) was added and the mixture was stirred at RT for 45 min. Then, the solvent was removed and the residue redissolved in EtOAc, washed with sat NaHCO3, water and dried over Na2SO4. The residue was purified by silica gel chromatography (25-35% EtOAc in hexanes) to give the title compound as a white solid. MS (ESI, positive ion) m/z: 306 (M+H).

후처리

  1. additionwas added
  2. customThen, the solvent was removed
  3. dissolutionthe residue redissolved in EtOAc
  4. washwashed
  5. dry with materialdried over Na2SO4
  6. customThe residue was purified by silica gel chromatography (25-35% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-f2c24425ee0f4b778565f1a525ae121d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476297B2

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