Trifluoroacetic acid → HCID 57941444, compound

HRID 1437881Notes

Reaction equation

HRID 1437881 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:15][N:16]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[F:36])[C:17]([CH:19]1[C:24](=O)[C@:23]2([CH3:29])[C:26]([CH3:28])([CH3:27])[C@H:20]1[CH2:21][CH2:22]2)=[O:18])=O)(C)(C)C>ClCCl>[F:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[N:16]1[C:17](=[O:18])[C:19]2[C@H:20]3[C:26]([CH3:28])([CH3:27])[C@:23]([CH3:29])([CH2:22][CH2:21]3)[C:24]=2[NH:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57941331HCID 57941331, compound

Product 1

HCID 57941444HCID 57941444, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic acid (10 mL) was added slowly to a cooled (0° C.) solution of N′-(2-fluoro-phenyl)-N′-((1S,4S)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carbonyl)-hydrazinecarboxylic acid tert-butyl ester (˜5.3 mmol) in dichloromethane (10 mL), and the resulting solution was stirred at 0° C. for 10 min and then at room temperature for 3.5 h. The solvent was evaporated and dichloromethane (80 mL) was added. The solution was washed with water (4×20 mL) and brine (20 mL), dried (magnesium sulfate), filtered, and evaporated to give an orange foam. This was triturated with 10% ethyl acetate/hexane (25 mL) and the mixture was cooled in an ice-bath at 0° C. for 1 h. The solid was filtered off and dried to give (4R,7S)-2-(2-fluoro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (890 mg, 58%) as a pale yellow solid.

Workup

  1. waitat room temperature for 3.5 h
  2. customThe solvent was evaporated
  3. additiondichloromethane (80 mL) was added
  4. washThe solution was washed with water (4×20 mL) and brine (20 mL)
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated
  8. customto give an orange foam
  9. customThis was triturated with 10% ethyl acetate/hexane (25 mL)
  10. temperaturethe mixture was cooled in an ice-bath at 0° C. for 1 h
  11. filtrationThe solid was filtered off
  12. customdried

Sources & evidence

ORD record
ord-c033227e38954781977cbb62ab5fa3e0
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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