HCID 70970333, compound → HCID 86677133, compound

HRID 1771889Notes

Reaction equation

HRID 1771889 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:14])=[C:6]([CH2:8][C@@H:9]([N:11]=[N+]=[N-])[CH3:10])[CH:7]=1>CCOC(C)=O.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:14])=[C:6]([CH2:8][C@@H:9]([NH2:11])[CH3:10])[CH:7]=1

Participants

4

Reactant 1

HCID 70970333HCID 70970333, compound

Product 1

HCID 86677133HCID 86677133, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1S)-2-(5-chloro-2-methylphenyl)-1-methylethyl azide (500 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 20 min. 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)-2-(5-chloro-2-methylphenyl)-1-methylethylamine (210 mg, 48%) as pale oil. ESI-MS: m/z (MH+) 184.4. 1H NMR (300 MHz, CDCl3): δ 7.12 (s, 1H), 7.08 (s, 2H), 3.16 (m, 1H), 2.48-2.70 (m, 2H), 2.28 (s, 3H), 1.23 (s, 2H), 1.13 (d, J=6.21 Hz, 3H).

Workup

  1. customfor 20 min
  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-84cc60e4df9b4b4aaa3b01fa10b74656
Source dataset
uspto-grants-2016_02
Patent number
US09249147B2

Reaction notes

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