Trifluoroacetic acid → (4r,7s)-2-(2-Chloro-4-fluoro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one
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]1Participants
Conditions
- Temperature
- 0 °C
Procedure
Trifluoroacetic acid (15 mL) was added in two portions to a cooled (0° C.) solution of N′-(2-chloro-4-fluoro-phenyl)-N′-((1S,4S)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carbonyl)-hydrazinecarboxylic acid tert-butyl ester (˜7.2 mmol) in dichloromethane (15 mL). The reaction mixture was stirred at 0° C. for 5 min and then at room temperature for 2 h. The reaction mixture was evaporated (using high vacuum in the end). Dichloromethane (100 mL) was added to the residue and the solution was washed with water (4×50 mL), and brine (50 mL), dried (magnesium sulfate), filtered, and evaporated to give (4R,7S)-2-(2-chloro-4-fluoro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (2.6 g, 113% of the expected amount) as a tan solid. This was used directly in subsequent steps without further purification.
Workup
- waitat room temperature for 2 h
- customThe reaction mixture was evaporated (
- additionDichloromethane (100 mL) was added to the residue
- washthe solution was washed with water (4×50 mL), and brine (50 mL)
- dry with materialdried (magnesium sulfate)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-1216b45ad47942559430940567505a58
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07622492B2
Reaction notes
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