Trifluoroacetic acid → HCID 178479887, compound

HRID 1437949Notes

Reaction equation

HRID 1437949 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 57941479HCID 57941479, compound

Product 1

HCID 178479887HCID 178479887, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added to a solution of (4S,7R)-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 (210 mg, 0.35 mmol) in dichloromethane (2 mL) and the resulting solution was stirred at room temperature for 3.5 h. Triethylsilane (56 μL, 0.35 mmol) was added and the solution was stirred for 5 min, and then evaporated and held under high vacuum overnight. The residue was taken up in dichloromethane and water and the pH was adjusted to ˜7 by adding saturated sodium bicarbonate solution. The layers were separated and the organic layer was dried (magnesium sulfate), filtered, evaporated, and chromatographed, eluting with 1-3% methanol/ethyl acetate to give (4S,7R)-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 (86 mg, 69%). ES(+)-MS (M+H) 355.

Workup

  1. stirringthe solution was stirred for 5 min
  2. customevaporated
  3. customheld under high vacuum overnight
  4. additionby adding saturated sodium bicarbonate solution
  5. customThe layers were separated
  6. dry with materialthe organic layer was dried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated
  9. customchromatographed
  10. washeluting with 1-3% methanol/ethyl acetate

Sources & evidence

ORD record
ord-f66673a098a64fc782033fa564d4d23c
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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