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

HRID 445285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 445285
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-f2c24425ee0f4b778565f1a525ae121d
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476297B2

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