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

HRID 1437894Notes

Reaction equation

HRID 1437894 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:15][N:16]([C:30]1[CH:35]=[C:34]([Cl:36])[CH:33]=[C:32]([Cl:37])[CH:31]=1)[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:34]1[CH:35]=[C:30]([N:16]2[C:17](=[O:18])[C:19]3[C@@H:20]4[C:26]([CH3:28])([CH3:27])[C@@:23]([CH3:29])([CH2:22][CH2:21]4)[C:24]=3[NH:15]2)[CH:31]=[C:32]([Cl:37])[CH:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57941408N'-(3,5-dichloro-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 57941373(4s,7r)-2-(3,5-Dichloro-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 (15 mL) was added in one portion to a cooled (0° C.) solution of N′-(3,5-dichloro-phenyl)-N′-((1R,4R)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carbonyl)-hydrazinecarboxylic acid tert-butyl ester (˜0.19 mmol) in dichloromethane (15 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 then under high vacuum. Dichloromethane (200 mL) was added. The solution was washed with water (4×125 mL), and brine (100 mL), dried (magnesium sulfate), filtered, evaporated, and dried overnight under high vacuum to give (4S,7R)-2-(3,5-dichloro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (7.2 g, 108% 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
  5. additionDichloromethane (200 mL) was added
  6. washThe solution was washed with water (4×125 mL), and brine (100 mL)
  7. dry with materialdried (magnesium sulfate)
  8. filtrationfiltered
  9. customevaporated
  10. customdried overnight under high vacuum

Sources & evidence

ORD record
ord-f098fa42fe1c4709a5b71bb64431a486
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

Loading…