Trifluoroacetic acid → HCID 57941345, compound

HRID 1437900Notes

Reaction equation

HRID 1437900 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[NH:16][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>[CH2:30]([N:15]1[C:24]2[C@:23]3([CH3:29])[C:26]([CH3:28])([CH3:27])[C@@H:20]([CH2:21][CH2:22]3)[C:19]=2[C:17](=[O:18])[NH:16]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57941364HCID 57941364, compound

Product 1

HCID 57941345HCID 57941345, compoundYield 7.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic acid (25.5 mL) was added to a solution of N-benzyl-N′-((1S,4S)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carbonyl)-hydrazinecarboxylic acid tert-butyl ester (˜30 mmol) in dichloromethane (25.5 mL) at 0° C. The reaction mixture was stirred at 0° C. for 30 min, at room temperature for 2 h, heated in a flak equipped with a reflux condenser at an oil-bath temperature of 80° C. for 6 h, and then at an oil-bath temperature of 100° C. overnight in the presence of molecular sieves. The molecular sieves were filtered off and washed with dichloromethane. The filtrate was washed with water until the washings were neutral. The organic layer was dried (sodium sulfate), filtered, evaporated, and purified using a Biotage system with a 330 g column, eluting with 2-5% methanol/dichloromethane, to give (4R,7S)-1-benzyl-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (610 mg, 7%) as a yellow solid.

Workup

  1. temperatureheated in a flak
  2. customequipped with a reflux condenser at an oil-bath temperature of 80° C. for 6 h
  3. customtemperature of 100° C. overnight
  4. filtrationThe molecular sieves were filtered off
  5. washwashed with dichloromethane
  6. washThe filtrate was washed with water until the washings
  7. dry with materialThe organic layer was dried (sodium sulfate)
  8. filtrationfiltered
  9. customevaporated
  10. custompurified
  11. washeluting with 2-5% methanol/dichloromethane

Sources & evidence

ORD record
ord-fadacd77b48642a49826b08be8fb86fd
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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