Trifluoroacetic acid → HCID 57941342, compound

HRID 1437898Notes

Reaction equation

HRID 1437898 reaction equation
FC(F)(F)C(O)=O.C(O[C:13]([N:15](C)[NH:16][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>[CH3:13][N:15]1[C:24]2[C@:23]3([CH3:29])[C:26]([CH3:28])([CH3:27])[C@@H:20]([CH2:21][CH2:22]3)[C:19]=2[C:17](=[O:18])[NH:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57941411HCID 57941411, compound

Product 1

HCID 57941342HCID 57941342, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic acid (15.7 mL) was added to a solution of N-methyl-N′-((1S,4S)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carbonyl)-hydrazinecarboxylic acid tert-butyl ester (6.13 g, 18.9 mmol) in dichloromethane (15.7 mL) at 0° C. The reaction mixture was stirred at 0° C. for 30 min, at room temperature for 1 h, and then heated at reflux for 6 h. Following overnight stirring at room temperature, the solvent was evaporated. The residue was taken up in dichloromethane (100 mL) and washed with water (2×100 mL) and brine (100 mL), dried (sodium sulfate), filtered, evaporated and purified using a Biotage system eluting with 2% methanol/dichloromethane to give (4R,7S)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (2.46 g, 63%) as a white solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 h
  3. waitFollowing overnight
  4. stirringstirring at room temperature
  5. customthe solvent was evaporated
  6. washwashed with water (2×100 mL) and brine (100 mL)
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. customevaporated
  10. custompurified
  11. washeluting with 2% methanol/dichloromethane

Sources & evidence

ORD record
ord-5fe6d58ae7284dfe839b8f6eeed5b290
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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