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

HRID 2194845Notes

Reaction equation

HRID 2194845 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-3f8fd0c45eec4de28e493b15f9747047
Source dataset
uspto-grants-2012_12
Patent number
US08334317B2

Reaction notes

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