Trifluoroacetic acid → HCID 178479886, compound

HRID 1438083Notes

Reaction equation

HRID 1438083 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]1[C:17]2[C@:16]3([CH3:21])[C:18]([CH3:20])([CH3:19])[C@@H:13]([CH2:14][CH2:15]3)[C:12]=2[C:11](=[O:22])[N:10]1[CH2:23][C:24]1[C:25]([C:48]([F:51])([F:50])[F:49])=[N:26][N:27](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:28]=1.C([SiH](CC)CC)C>ClCCl>[CH3:8][N:9]1[C:17]2[C@:16]3([CH3:21])[C:18]([CH3:19])([CH3:20])[C@@H:13]([CH2:14][CH2:15]3)[C:12]=2[C:11](=[O:22])[N:10]1[CH2:23][C:24]1[C:25]([C:48]([F:49])([F:50])[F:51])=[N:26][NH:27][CH:28]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57941494HCID 57941494, compound

Product 1

HCID 178479886HCID 178479886, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (4 mL) was added to a solution of (4R,7S)-1,7,8,8-tetramethyl-2-(3-trifluoromethyl-1-trityl-1H-pyrazol-4-ylmethyl)-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (410 mg, 0.69 mmol) in dichloromethane (4 mL) and the yellow solution was stirred at room temperature for 4 h. Triethylsilane (110 μL, 0.69 mmol) was added and the solution was stirred at room temperature for 10 min. The solvent was evaporated using a rotary evaporator and the residue was held under high vacuum overnight. The residue was taken up in dichloromethane (50 mL), the solution was transferred to a separatory funnel and water (50 mL) was added. Aqueous saturated sodium hydrogen carbonate (1 Pasteur pipette) was added and the layers were separated. The organic layer was washed with brine (50 mL), dried (magnesium sulfate), filtered, evaporated, and purified using a Biotage 40S system, eluting with 1-3% methanol/ethyl acetate, to give (4R,7S)-1,7,8,8-tetramethyl-2-(3-trifluoromethyl-1H-pyrazol-4-ylmethyl)-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (118 mg, 48%) as an off-white solid. APCI(+)-MS (M+H) 355.

Workup

  1. stirringthe solution was stirred at room temperature for 10 min
  2. customThe solvent was evaporated
  3. customa rotary evaporator
  4. customwas held under high vacuum overnight
  5. customthe solution was transferred to a separatory funnel
  6. additionwater (50 mL) was added
  7. additionAqueous saturated sodium hydrogen carbonate (1 Pasteur pipette) was added
  8. customthe layers were separated
  9. washThe organic layer was washed with brine (50 mL)
  10. dry with materialdried (magnesium sulfate)
  11. filtrationfiltered
  12. customevaporated
  13. custompurified
  14. washeluting with 1-3% methanol/ethyl acetate

Sources & evidence

ORD record
ord-3569786fb42b41158f129cda06825d87
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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