Trifluoroacetic acid → HCID 11206513, compound

HRID 1369907Notes

Reaction equation

HRID 1369907 reaction equation
C(OC([N:8]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH:11]2[CH2:18][CH2:19][CH2:20][C:10]2([F:21])[C:9]1=[O:22])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.O.C(OCC)(=O)C>[F:21][C:10]12[CH2:20][CH2:19][CH2:18][CH:11]1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=1[NH:8][C:9]2=[O:22]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18516376HCID 18516376, compound

Product 1

HCID 11206513HCID 11206513, compoundYield 70.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 350 mg (1.1 mmol) of 5-tert-butoxycarbonyl-3a-fluoro-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one in 5 mL of dichloromethane is mixed with 5 ml of trifluoroacetic acid at room temperature. After 1 hour, the batch is diluted with water (100 ml) and ethyl acetate (100 ml). The organic phase is separated, washed with water (50 ml), saturated NaHCO3, (2×50 ml) and saturated NaCl (50 ml), dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography of the residue on silica gel with hexane-ethyl acetate yields 160 mg of product.

Workup

  1. customThe organic phase is separated
  2. washwashed with water (50 ml), saturated NaHCO3, (2×50 ml) and saturated NaCl (50 ml)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-266d6f04e3244f7d9703b6b169ab2ebc
Source dataset
uspto-grants-2003_06
Patent number
US06579883B1

Reaction notes

Loading…