Pyrrolidine, 1-(2-(4-(2,2-dimethyl-7-methoxy-3-phenyl-2H-1-benzopyran-4-yl)phenoxy)ethyl)- → HCID 10895762, compound

HRID 582819Notes

Reaction equation

HRID 582819 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)=[CH:23][CH:22]=3)=[C:8]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]([CH3:14])([CH3:13])[O:10]2)=[CH:5][CH:4]=1.[H][H]>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C@H:7]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)=[CH:25][CH:26]=3)[C@H:8]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]([CH3:14])([CH3:13])[O:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 421182Pyrrolidine, 1-(2-(4-(2,2-dimethyl-7-methoxy-3-phenyl-2H-1-benzopyran-4-yl)phenoxy)ethyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 10895762HCID 10895762, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

7-Methoxy-2,2-dimethyl-3-phenyl-4-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}-3-chromene (25 g) was dissolved in acetic acid (250 ml) at 60° C. Palladium on carbon (2.5 g, 10%, 50% wet) was added and the mixture hydrogenated at 1 atmosphere hydrogen pressure at 60° C. for 24 hours. The catalyst was filtered off and the filtrate evaporated to en oil. The oil was dissolved in toluene (100 ml) and washed with sodium hydroxide solution (4M) until alkaline. The aqueous phase was separated and extracted with another portion of toluene (20 ml). The combined organic phases was washed with water (2×50 ml) and evaporated to an oil. The oil was dissolved in methanol (100 ml) and crystallized by adding water (200 ml). The product was filtered off and dried.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated to en oil
  3. dissolutionThe oil was dissolved in toluene (100 ml)
  4. washwashed with sodium hydroxide solution (4M) until alkaline
  5. customThe aqueous phase was separated
  6. extractionextracted with another portion of toluene (20 ml)
  7. washThe combined organic phases was washed with water (2×50 ml)
  8. customevaporated to an oil
  9. dissolutionThe oil was dissolved in methanol (100 ml)
  10. customcrystallized
  11. additionby adding water (200 ml)
  12. filtrationThe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-bd4c0ee3ae7b4189b636ae7e5172bba2
Source dataset
uspto-grants-1999_07
Patent number
US05925771

Reaction notes

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