Ammonium Carbonate → HCID 10293759, compound

HRID 1267873Notes

Reaction equation

HRID 1267873 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@H:13]2[CH2:27][O:26][C:16]3[CH:17]=[CH:18][C:19]4[C:20](=[O:25])[CH:21]=[CH:22][O:23][C:24]=4[C:15]=3[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[NH4+].[NH4+]>CO.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH:13]2[CH2:27][O:26][C:16]3[CH:17]=[CH:18][C:19]4[C:20](=[O:25])[CH2:21][CH2:22][O:23][C:24]=4[C:15]=3[O:14]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 517111Ammonium CarbonateHCID 11292172HCID 11292172, compound

Product 1

HCID 10293759HCID 10293759, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.50 g (1.28 mmole) of [(2R)-7-oxo-2,3-dihydro-7H-[1,4]dioxino[2,3-h]chromen-2-yl]methyl 4-methylbenzenesulfonate in methanol was added to a round bottom flask containing 0.40 g of 10% palladium on carbon under a stream of nitrogen, ammonium carbonate was then added and the heterogeneous mixture was heated to reflux for 2.5 hours. After the catalyst was removed by filtration, the filtrate was concentrated in vacuum and the residue column chromatographed on silica gel with 0.5% methanol/methylene chloride as eluant to give 0.30 g (61%) of the (R)-enantiomer of the title compound as a white foam. 1H (CDCl3) doublet 7.8 δ (2 H); doublet 7.5 δ (1 H); doublet 7.4 δ (2 H); doublet 6.6 δ (1 H); triplet 4.6 δ (2 H); multiplet 4-4.5 δ (5 H); triplet 2.8 δ (2 H); singlet 2.5 δ (3 H).

Workup

  1. additionwas then added
  2. temperaturethe heterogeneous mixture was heated
  3. temperatureto reflux for 2.5 hours
  4. customAfter the catalyst was removed by filtration
  5. concentrationthe filtrate was concentrated in vacuum
  6. customthe residue column chromatographed on silica gel with 0.5% methanol/methylene chloride as eluant

Sources & evidence

ORD record
ord-efbe97bebd8844f78bd7fe346982ff62
Source dataset
uspto-grants-2003_04
Patent number
US06555560B2

Reaction notes

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