Ammonium formate → HCID 58400517, compound

HRID 1673179Notes

Reaction equation

HRID 1673179 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C@H:12]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[O:13]1)[CH:6]=[CH:5]2.C([O-])=O.[NH4+]>C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C@H:12]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[O:13]1)[CH2:6][CH2:5]2

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 58400514HCID 58400514, compound

Product 1

HCID 58400517HCID 58400517, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A 75:25 diastereoisomeric mixture of 6-fluoro-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2H-chromene (50 mg, 0.18 mmol, 90.4% A) was dissolved in ethanol and stirred under nitrogen athmosphere at 25° C. Ammonium formiate (60.5 mg, 0.96 mmol) and 10% palladium on carbon (50 mg) were added to the stirred solution and the reaction mixture refluxed for 15 h. The reaction mixture was checked to show complete conversion of the starting material. The solids were removed by filtration and the filtrate was concentrated under reduced pressure to furnish 6-fluoro-3,4-dihydro-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2H-chromene (40 mg, 0.115 mmol, 72.6% A, 64% yield) as a 75:25 mixture of diastereoisomers.

Workup

  1. temperaturethe reaction mixture refluxed for 15 h
  2. customThe solids were removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-93ec45ff052e4499be8bf2744fc0ab2e
Source dataset
uspto-grants-2011_08
Patent number
US07999124B2

Reaction notes

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