(+)-1-(1-Naphthyl)ethylamine → (1R)-1-(1-naphthyl)-N-({1-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}methyl)ethanamine

HRID 2194845Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194845
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][C:11]([CH:14]=O)=[N:10]2)=[CH:5][CH:4]=1.[C:18]1([C@H:28]([NH2:30])[CH3:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CC(O)=O.ClCCCl>[C:18]1([C@H:28]([NH:30][CH2:14][C:11]2[CH:12]=[CH:13][N:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:17])([F:16])[F:1])=[CH:4][CH:5]=3)[N:10]=2)[CH3:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1

Komponenten

6

Edukt 3

HCID 2724264(+)-1-(1-Naphthyl)ethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 574169821-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbaldehyde

Produkt 1

HCID 25263532(1R)-1-(1-naphthyl)-N-({1-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}methyl)ethanamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

A 20 mL vial was charged with 1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbaldehyde 65 (0.200 g, 0.833 mmol), (R)-1-(naphthalen-1-yl)ethanamine 39 (0.171 g, 0.999 mmol), sodium triacetoxyborohydride (0.353 g, 1.67 mmol), 4 mL of DCE, and 3 drops of AcOH. This mixture was stirred overnight at room temperature and then quenched with saturated aqueous NaHCO3. The mixture was extracted with DCM, dried, and concentrated. Purification by column chromatography on silica gel (10% to 50% EtOAc in hexanes) gave ((1R)-1-(1-naphthyl)-N-({1-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}methyl)ethanamine 66. Mass spectrum, calculated for C23H20F3N3 395.2; found 396.2 (M++1).

Aufarbeitung

  1. customquenched with saturated aqueous NaHCO3
  2. extractionThe mixture was extracted with DCM
  3. customdried
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel (10% to 50% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3f8fd0c45eec4de28e493b15f9747047
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334317B2

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