Sodium Bicarbonate → HCID 21072012, compound

HRID 1372497Notes

Reaction equation

HRID 1372497 reaction equation
C([NH:4][C:5]1[CH:17]=[C:16]2[C:8]([C:9]3[C:14]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:15]2)[CH2:13][CH2:12][C:11](=[O:22])[CH:10]=3)=[CH:7][CH:6]=1)(=O)C.C([O-])(O)=O.[Na+]>CO.Cl.CCOC(C)=O>[NH2:4][C:5]1[CH:17]=[C:16]2[C:8]([C:9]3[C:14]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:15]2)[CH2:13][CH2:12][C:11](=[O:22])[CH:10]=3)=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 516892Sodium Bicarbonate2×HCID 21072009HCID 21072009, compound

Product 1

HCID 21072012HCID 21072012, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

The crude product from step 3 (7.0 g) was dissolved in MeOH (100 mL) and the solution was diluted with 6N HCl (100 mL). The resulting brown solution was stirred and heated in an oil bath at 80° C. for one hour. After cooling, the mixture was diluted with EtOAc (300 mL), stirred, and neutralized by the careful addition of aqueous 5% NaHCO3 and solid NaHCO3. The layers were separated and the aqueous portion was extracted with EtOAc (100 mL). The combined organics were washed with water and brine, dried over MgSO4, filtered, and concentrated under vacuum to an orange-red solid. The crude product was purified by Biotage flash chromatography on a 75 L silica gel column (7.5×35 cm), eluting with 2:1 hexane-EtOAc. The product-containing fractions were evaporated under vacuum to an orange solid (4.2 g) which was shown by 1H NMR to contain 7-amino-9a-butyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one along with approximately 10% of the 9a-butyl-4-methyl-8,9,9a,10-tetrahydro-7H-indenol[1,2-g]quinolin-7-one by-product. This material was used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. stirringstirred
  3. customThe layers were separated
  4. extractionthe aqueous portion was extracted with EtOAc (100 mL)
  5. washThe combined organics were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum to an orange-red solid
  9. customThe crude product was purified by Biotage flash chromatography on a 75 L silica gel column (7.5×35 cm)
  10. washeluting with 2:1 hexane-EtOAc
  11. customThe product-containing fractions were evaporated under vacuum to an orange solid (4.2 g) which
  12. customThis material was used in the next step without further purification

Sources & evidence

ORD record
ord-6300da5774a943c89a7fcc20f7353ce9
Source dataset
uspto-grants-2007_01
Patent number
US07157604B2

Reaction notes

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