Trifluoroacetic acid → 3a-Fluoro-7-(2-furanyl)-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one

HRID 1369918Notes

Reaction equation

HRID 1369918 reaction equation
C(OC([N:8]1[C:17]2[CH:16]=[C:15]([C:18]3[O:19][CH:20]=[CH:21][CH:22]=3)[CH:14]=[CH:13][C:12]=2[CH:11]2[CH2:23][CH2:24][CH2:25][C:10]2([F:26])[C:9]1=[O:27])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.O.C(OCC)(=O)C>[F:26][C:10]12[CH2:25][CH2:24][CH2:23][CH:11]1[C:12]1[CH:13]=[CH:14][C:15]([C:18]3[O:19][CH:20]=[CH:21][CH:22]=3)=[CH:16][C:17]=1[NH:8][C:9]2=[O:27]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 185163745-Tert-butoxycarbonyl-3a-fluoro-7-(2-furanyl)-1,2,3,3a,5,9b-hexahydrocyclopenta[c]-quinolin-4-one

Product 1

HCID 185163563a-Fluoro-7-(2-furanyl)-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-oneYield 50.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.44 g (3.9 mmol) of 5-tert-butoxycarbonyl-3a-fluoro-7-(2-furanyl)-1,2,3,3a,5,9b-hexahydrocyclopenta[c]-quinolin-4-one in 20 ml of dichloromethane is mixed with 8 ml of trifluoroacetic acid at room temperature. After 2 hours, the batch is diluted with water and ethyl acetate. The organic phase is separated, washed with water, saturated NaHCO3 and saturated NaCl, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography of the residue on silica gel with hexane-ethyl acetate yields 0.53 g of product.

Workup

  1. customThe organic phase is separated
  2. washwashed with water, saturated NaHCO3 and saturated NaCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-cbdfce6d4a5a4443a23c075fefc0b1eb
Source dataset
uspto-grants-2003_06
Patent number
US06579883B1

Reaction notes

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