HCID 70970404, compound → HCID 86677134, compound

HRID 2409492Notes

Reaction equation

HRID 2409492 reaction equation
[F:1][C:2]1[C:3]([CH3:15])=[C:4]([CH2:9][C@@H:10]([N:12]=[N+]=[N-])[CH3:11])[CH:5]=[CH:6][C:7]=1[F:8]>CCOC(C)=O.[Pd]>[F:1][C:2]1[C:3]([CH3:15])=[C:4]([CH2:9][C@@H:10]([NH2:12])[CH3:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 1

HCID 70970404HCID 70970404, compound

Product 1

HCID 86677134HCID 86677134, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1S)-2-(3,4-difluoro-2-methylphenyl)-1-methylethyl azide (503 mg, 2.38 mmol) in 50 mL of EtOAc was added Pd/C (150 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 silica gel 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)-2-(3,4-difluoro-2-methylphenyl)-1-methylethylamine (376 mg, 85%) as pale oil. ESI-MS: m/z (MH+) 186.4. 1H NMR (300 MHz, CDCl3): δ 6.82-6.97 (m, 2H), 3.12 (m, 1H), 2.48-2.73 (m, 2H), 2.25 (s, 3H), 1.34 (s, 2H), 1.12 (d, J=6.39 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-91170512f9044d8182265a132176c46f
Source dataset
uspto-grants-2014_08
Patent number
US08815906B2

Reaction notes

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