Trifluoroacetic acid → HCID 57941362, compound

HRID 1437866Notes

Reaction equation

HRID 1437866 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13]([N:15]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[Cl:36])[NH:16][C:17]([CH:19]1[C:24](=O)[C@@:23]2(C)[C:26]([CH3:28])([CH3:27])[C@@H:20]1[CH2:21][CH2:22]2)=O)=O)(C)(C)C>ClCCl>[Cl:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[N:15]1[C:13](=[O:12])[C:19]2[C@@H:20]3[C:26]([CH3:28])([CH3:27])[C@@:23]([CH3:24])([CH2:22][CH2:21]3)[C:17]=2[NH:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69018628HCID 69018628, compound

Product 1

HCID 57941362HCID 57941362, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (55 mL) was added slowly over 1-2 min to a solution of N-(2-chloro-phenyl)-N′-((1R,4R)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carbonyl)-hydrazinecarboxylic acid tert-butyl ester (23.4 g, 56 mmol) in dry dichloromethane (55 mL), and the resulting solution was stirred at room temperature for 3 h. The solvent was evaporated and dichloromethane (350 mL) was added. The solution was washed with water (3×150 mL) and brine (150 mL), dried (sodium sulfate), filtered, evaporated, and dried under high vacuum over the weekend to give (4S,7R)-2-(2-chloro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (16.07 g, 95%) as a pale solid.

Workup

  1. customThe solvent was evaporated
  2. additiondichloromethane (350 mL) was added
  3. washThe solution was washed with water (3×150 mL) and brine (150 mL)
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. customdried under high vacuum over the weekend

Sources & evidence

ORD record
ord-887a64e545e64fcaa1c6c1dbf074b096
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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