Trifluoroacetic acid → HCID 18516371, compound

HRID 1369912Notes

Reaction equation

HRID 1369912 reaction equation
C(OC([N:8]1[C:17]2[CH:16]=[CH:15][C:14]([Br:18])=[CH:13][C:12]=2[CH:11]2[CH2:19][CH2:20][CH2:21][C:10]2([F:22])[C:9]1=[O:23])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.O.C(OCC)(=O)C>[Br:18][C:14]1[CH:15]=[CH:16][C:17]2[NH:8][C:9](=[O:23])[C:10]3([F:22])[CH2:21][CH2:20][CH2:19][CH:11]3[C:12]=2[CH:13]=1

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18516357HCID 18516357, compound

Product 1

HCID 18516371HCID 18516371, compoundYield 72.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.38 g (3.6 mmol) of 5-tert-butoxycarbonyl-8-bromo-3a-fluoro-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one in 7 ml of dichloromethane is mixed with 7 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 0.74 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-0be21560fdba4f119bb8e0986d51451b
Source dataset
uspto-grants-2003_06
Patent number
US06579883B1

Reaction notes

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