1-Phenethylamine, (+)- → HCID 25263535, compound

HRID 2194850Notes

Reaction equation

HRID 2194850 reaction equation
[C:1]1([C@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][O:11][C:12]1[N:16]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[N:15]=[C:14]([CH:27]=O)[CH:13]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CC(O)=O.ClCCCl>[CH3:10][O:11][C:12]1[N:16]([C:17]2[CH:18]=[CH:19][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:21][CH:22]=2)[N:15]=[C:14]([CH2:27][NH:9][C@@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:8])[CH:13]=1

Participants

6

Reactant 3

HCID 6431891-Phenethylamine, (+)-HCID 5049666Sodium triacetoxyborohydrideHCID 58360612HCID 58360612, compound

Product 1

HCID 25263535HCID 25263535, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A 20 mL vial was charged with (R)-1-phenylethanamine 45 (0.135 g, 1.11 mmol), 5-methoxy-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbaldehyde 74 (0.200 g, 0.740 mmol), 5 mL of DCE, 3 drops of concentrated AcOH, and sodium triacetoxyborohydride (0.314 g, 1.48 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with 10 mL of saturated aqueous NaHCO3 and the mixture was extracted with CH2Cl2. The combined extracts were dried and concentrated. Purification via column chromatography on silica gel (1% to 6% MeOH in DCM) gave (1R)—N-({5-methoxy-1-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}methyl)-1-phenylethanamine 75. Mass spectrum: calculated for C20H20F3N3O 375.2; found 376.2 (M++1).

Workup

  1. customThe reaction mixture was quenched with 10 mL of saturated aqueous NaHCO3
  2. extractionthe mixture was extracted with CH2Cl2
  3. customThe combined extracts were dried
  4. concentrationconcentrated
  5. customPurification via column chromatography on silica gel (1% to 6% MeOH in DCM)

Sources & evidence

ORD record
ord-3bcedc2767de49e4b7e84e09b4cbf661
Source dataset
uspto-grants-2012_12
Patent number
US08334317B2

Reaction notes

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