HCID 66718591, compound → HCID 66718751, compound

HRID 1690806Notes

Reaction equation

HRID 1690806 reaction equation
C([O:8][CH2:9][CH:10]1[CH2:23][O:22][C:13]2=[N:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=[C:12]2[O:11]1)C1C=CC=CC=1>C(O)C.[Pd]>[F:21][C:18]([F:19])([F:20])[C:15]1[N:14]=[C:13]2[O:22][CH2:23][CH:10]([CH2:9][OH:8])[O:11][C:12]2=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 66718591HCID 66718591, compound

Product 1

HCID 66718751HCID 66718751, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 2-benzyloxymethyl-6-trifluoromethyl-2,3-dihydro[1,4]dioxino[2,3-b]pyridine (420 mg, 1.3 mmol) in ethanol (50 mL) was added 10% palladium on carbon (10 mg, cat.). The reaction mixture was evacuated and purged with hydrogen six times, then stirred for 3 hours under a hydrogen atmosphere. The reaction mixture was filtered through celite, washing with EtOH (60 mL), and the filtrate evaporated to dryness. Trituration using DCM/hexanes gave the title compound (250 mg, 78%) as a solid. m/z=236.2 (M+1), r.t.=2.46 mins. 1H NMR (400 MHz; CDCl3) δ7.38-7.28 (2H, m), 4.50-4.46 (1H, m), 4.41 (1H, dd), 4.20 (1H, dd), 4.04 (1H, dd), 3.90 (1H, dd).

Workup

  1. customThe reaction mixture was evacuated
  2. custompurged with hydrogen six times
  3. filtrationThe reaction mixture was filtered through celite
  4. washwashing with EtOH (60 mL)
  5. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-c6371fd7945b4d1686952bc3e8308366
Source dataset
uspto-grants-2012_04
Patent number
US08153651B2

Reaction notes

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