HCID 57791810, compound → HCID 57791826, compound

HRID 1091716Notes

Reaction equation

HRID 1091716 reaction equation
[F:1][CH2:2][CH:3]([O:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)[CH2:4][F:5]>CO.[Rh]>[F:5][CH2:4][CH:3]([O:6][CH:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]1)[CH2:2][F:1]

Participants

4

Reactant 1

HCID 57791810HCID 57791810, compound

Product 1

HCID 57791826HCID 57791826, compoundYield 80,275.398%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

4-(1,3-difluoropropan-2-yloxy)pyridine (27) (0.098 mg, 0.57 μmol) and 5% rhodium on alumina (0.02 g, 2.56 μmol) in MeOH (50 mL) were stirred under an atmosphere of hydrogen at 5 bar and 25° C. for 16 hours. The catalyst was filtered and washed with MeOH and the solvent evaporated to afford the desired compound as a gum (0.082 g, 81%); 1H NMR (400.132 MHz, CDCl3) δ 1.43-1.48 (1H, m), 1.60-1.71 (1H, m), 1.82-2.15 (3H, m), 2.42 (1H, s), 2.84-2.92 (1H, m), 3.09-3.14 (1H, m), 3.25-3.30 (1H, m), 3.82-3.95 (1H, m), 4.35-4.44 (2H, m), 4.47-4.56 (2H, m).

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with MeOH
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-d4e023a8102043e5be79632a5b86ed37
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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