Trifluoroacetic acid → HCID 131734160, compound

HRID 717900Notes

Reaction equation

HRID 717900 reaction equation
[CH:1]1([CH:7]2[CH:16]3[CH2:17][CH2:18][CH2:19][O:20][CH:15]3[C:14]3[CH:13]=[C:12]([NH:21]C(=O)[O-])[CH:11]=[CH:10][C:9]=3[NH:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[CH:1]1([CH:7]2[CH:16]3[CH2:17][CH2:18][CH2:19][O:20][CH:15]3[C:14]3[CH:13]=[C:12]([NH2:21])[CH:11]=[CH:10][C:9]=3[NH:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 131734161HCID 131734161, compound

Product 1

HCID 131734160HCID 131734160, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of tert-butyl (4aSR*,5SR*,10bSR*)-5-cyclohexyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-9-ylcarbamate (prepared according to the method described in example 1) (227 mg, 0.587 mmol) in CH2Cl2 (5 mL) under argon atmosphere was added TFA (1.5 mL) dropwise. The reaction solution was allowed to reach r.t. and stirred overnight. The mixture was cooled down and 0.5 N NaOH solution was added until basic pH. The product was extracted with CH2Cl2 three times. The combined organic fractions were washed with sat. NaCl solution, dried over Na2SO4, and the solvent removed under reduced pressure after filtration giving (4aSR*,5SR*,10bSR*)-5-cyclohexyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-9-amine (145 mg, 86%) as orange viscous solid. The product was used without further purification.

Workup

  1. customprepared
  2. customto reach r.t.
  3. temperatureThe mixture was cooled down
  4. extractionThe product was extracted with CH2Cl2 three times
  5. washThe combined organic fractions were washed with sat. NaCl solution
  6. dry with materialdried over Na2SO4
  7. customthe solvent removed under reduced pressure
  8. filtrationafter filtration

Sources & evidence

ORD record
ord-0086c73c29bd418bb31c07fb86a6b4e0
Source dataset
uspto-grants-2015_11
Patent number
US09193738B2

Reaction notes

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