HCID 70970325, compound → HCID 66686477, compound

HRID 1771881Notes

Reaction equation

HRID 1771881 reaction equation
[CH3:1][C@H:2]([N:13]=[N+]=[N-])[CH2:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([F:11])[C:5]=1[F:12]>CCOC(C)=O.[Pd]>[CH3:1][C@H:2]([NH2:13])[CH2:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([F:11])[C:5]=1[F:12]

Participants

4

Reactant 1

HCID 70970325HCID 70970325, compound

Product 1

HCID 66686477HCID 66686477, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1S)-1-methyl-2-(2,3,5-trifluorophenyl)ethyl azide (930 mg, 4.32 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-(2,3,5-trifluorophenyl)ethylamine (475 mg, 58%) as pale yellow oil. ESI-MS: m/z (MH+) 190.1. 1H NMR (300 MHz, CDCl3): δ 7.04 (m, 1H), 6.83 (m, 1H), 4.06 (s, 2H), 3.42 (m, 1H), 2.92 (m, 2H), 1.29 (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-ec4c4dbbea9b43d2ba27ca0d77780229
Source dataset
uspto-grants-2016_02
Patent number
US09249147B2

Reaction notes

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