HCID 70970323, compound → HCID 70970416, compound

HRID 1771880Notes

Reaction equation

HRID 1771880 reaction equation
[CH3:1][C@H:2]([N:15]=[N+]=[N-])[CH2:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[CH3:14]>CCOC(C)=O.[Pd]>[CH3:1][C@H:2]([NH2:15])[CH2:3][C:4]1[CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=[CH:6][C:5]=1[CH3:14]

Participants

4

Reactant 1

HCID 70970323HCID 70970323, compound

Product 1

HCID 70970416HCID 70970416, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1S)-1-methyl-2-[2-methyl-5-(trifluoromethyl)phenyl]ethyl azide (1.64 g, 6.74 mmol) in 100 mL of EtOAc was added Pd/C (300 mg of 10% Pd) and the mixture was hydrogenated under hydrogen balloon for 1 h. The catalyst was removed by filtration through celite, then passed through silicagel plug eluting first with EtOAc (40 mL), then MeOH/EtOAc/NH4OH 20:75:5 (120 mL). The fraction with product was evaporated to give (1S)-1-methyl-2-[2-methyl-5-(trifluoromethyl)phenyl]ethylamine (1.10 g, 75%) as pale yellow oil. ESI-MS: m/z (MH+) 218.4. 1H NMR (300 MHz, CDCl3): δ 7.37 (m, 2H), 7.20 (m, 1H), 3.20 (m, 1H), 2.58-2.77 (m, 2H), 2.38 (s, 3H), 1.42 (s, 2H), 1.14 (d, J=6.21 Hz, 3H).

Workup

  1. customfor 1 h
  2. customThe catalyst was removed by filtration through celite
  3. washeluting first with EtOAc (40 mL)
  4. customThe fraction with product was evaporated

Sources & evidence

ORD record
ord-68c399b4772d41d48922bcd69d7f9812
Source dataset
uspto-grants-2016_02
Patent number
US09249147B2

Reaction notes

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