Trifluoroacetic acid → (4r,7s)-2-(2-Chloro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one

HRID 1437883Notes

Reaction equation

HRID 1437883 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[Cl: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>[Cl: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 57941450HCID 57941450, compound

Product 1

HCID 57941340(4r,7s)-2-(2-Chloro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-oneYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 mL) was added slowly to a solution of N′-(2-chloro-phenyl)-N′-((1S,4S)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carbonyl)-hydrazinecarboxylic acid tert-butyl ester (1.26 g, 3.0 mmol) in dichloromethane (5 mL), and the resulting solution was stirred at room temperature for 19 h. The solvent was evaporated and dichloromethane (100 mL) was added. The solution was washed with water (2×50 mL) and brine (50 mL), dried (sodium sulfate), filtered, and evaporated to give a light yellow solid. The solid was stored in the freezer over the weekend, and then triturated with 50% hexanes/diethyl ether (10 mL) and the mixture sonicated. The solid was collected by filtration, washed with ether, an air-dried to give (4R,7S)-2-(2-chloro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (790 mg, 86%) as an off-white solid.

Workup

  1. customThe solvent was evaporated
  2. additiondichloromethane (100 mL) was added
  3. washThe solution was washed with water (2×50 mL) and brine (50 mL)
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a light yellow solid
  8. customtriturated with 50% hexanes/diethyl ether (10 mL)
  9. customthe mixture sonicated
  10. filtrationThe solid was collected by filtration
  11. washwashed with ether
  12. customan air-dried

Sources & evidence

ORD record
ord-7770ce1c0a0d42de865fcd873e528622
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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