Sodium Carbonate → 2-(2-chlorophenyl)-5,7-dihydroxy-8-((2R,3S)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl)chromen-4-one

HRID 1363333Notes

Reaction equation

HRID 1363333 reaction equation
Cl.N1C=CC=CC=1.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[O:16][C:17]2[C:22]([C:23](=[O:25])[CH:24]=1)=[C:21]([O:26]C)[CH:20]=[C:19]([O:28]C)[C:18]=2[C@@H:30]1[CH2:34][CH2:33][N:32]([CH3:35])[C@H:31]1[CH2:36][OH:37].C([O-])([O-])=O.[Na+].[Na+]>CO>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[O:16][C:17]2[C:22]([C:23](=[O:25])[CH:24]=1)=[C:21]([OH:26])[CH:20]=[C:19]([OH:28])[C:18]=2[C@@H:30]1[CH2:34][CH2:33][N:32]([CH3:35])[C@H:31]1[CH2:36][OH:37]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10176127Pyridinium chlorideHCID 59318486(+)-trans-2-(2-Chloro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one

Product 1

HCID 236439762-(2-chlorophenyl)-5,7-dihydroxy-8-((2R,3S)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl)chromen-4-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
180 °C

Procedure

Molten pyridine hydrochloride (2.5 g, 21 mmol, 10×w/w) was added to compound of example 7 (0.25 g, 0.58 mmol) and heated at 180° C. for 1.5 h. The reaction mixture was cooled to 25° C., diluted with MeOH (10 mL) and basified using Na2CO3 to pH 10. The mixture was filtered and the organic layer was concentrated. The residue was suspended in water (10 mL), stirred for 30 min., filtered and dried to obtain the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to 25° C.
  2. filtrationThe mixture was filtered
  3. concentrationthe organic layer was concentrated
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-aca600141bb04cdaad081c923a9e9550
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

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