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

HRID 1437871Notes

Reaction equation

HRID 1437871 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:15][N:16]([C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=1[Cl:37])[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:37][C:31]1[CH:32]=[C:33]([F:36])[CH:34]=[CH:35][C:30]=1[N:16]1[C:17](=[O:18])[C:19]2[C@@H:20]3[C:26]([CH3:27])([CH3:28])[C@@:23]([CH3:29])([CH2:22][CH2:21]3)[C:24]=2[NH:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57941348N'-(2-chloro-4-fluoro-phenyl)-N'-((1R,4R)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carbonyl)-hydrazinecarboxylic acid tert-butyl ester

Product 1

HCID 57941321(4s,7r)-2-(2-Chloro-4-fluoro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic acid (50 mL) was added in two portions to a cooled (0° C.) solution of N′-(2-chloro-4-fluoro-phenyl)-N′-((1R,4R)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carbonyl)-hydrazinecarboxylic acid tert-butyl ester (14.8 g, 33.7 mmol) in dichloromethane (50 mL). The mixture was stirred at 0° C. for 5 min and then the cooling bath was removed and the reaction mixture was allowed to warm to room temperature and stir for 4 h. Volatiles were evaporated under reduced pressure and dichloromethane (250 mL) was added. The solution was washed with water (4×125 mL), and brine (125 mL), dried (magnesium sulfate), filtered, and evaporated. The flask containing the product was covered in foil and the solid was dried overnight under high vacuum to give (4S,7R)-2-(2-chloro-4-fluoro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (11.4 g, 105% of the expected amount). This material was used in subsequent reactions without further purification.

Workup

  1. customthe cooling bath was removed
  2. temperatureto warm to room temperature
  3. stirringstir for 4 h
  4. customVolatiles were evaporated under reduced pressure and dichloromethane (250 mL)
  5. additionwas added
  6. washThe solution was washed with water (4×125 mL), and brine (125 mL)
  7. dry with materialdried (magnesium sulfate)
  8. filtrationfiltered
  9. customevaporated
  10. additionThe flask containing the product
  11. customthe solid was dried overnight under high vacuum

Sources & evidence

ORD record
ord-1354372c18a6400dacaf86fe817e3761
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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