Trifluoroacetic acid → HCID 58930118, compound

HRID 2360278Notes

Reaction equation

HRID 2360278 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]23[CH2:18][CH2:17][C:14]([NH:19]C(=O)OC(C)(C)C)([CH2:15][CH2:16]2)[CH2:13][CH2:12]3)=[CH:7][CH:6]=1)(=[O:4])=[O:3].FC(F)(F)C(O)=O>O.C(Cl)Cl>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]23[CH2:18][CH2:17][C:14]([NH2:19])([CH2:15][CH2:16]2)[CH2:13][CH2:12]3)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58930151HCID 58930151, compound

Product 1

HCID 58930118HCID 58930118, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 100 mL round-bottomed flask equipped with magnetic stirring was added tert-butyl 4-(4-(methylsulfonyl)phenyl)bicyclo[2.2.2]octan-1-ylcarbamate (170 mg, 448 μmol), 2 mL of CH2Cl2, ca. 5 drops of water, and trifluoroacetic acid (2 mL, 27 mmol). The reaction mixture was stirred at ambient temperature for 3.5 h, after which time the mixture was concentrated in vacuo. NaOH (ca. 50 mL of a 1M aq. solution) was added to the mixture, and the aqueous layer was extracted with CH2Cl2 (3×15 mL). The organic layers were combined, dried over K2CO3, filtered, and concentrated in vacuo to give 4-(4-(methylsulfonyl)phenyl)bicyclo[2.2.2]octan-1-amine (mass=120 mg, Mass Spec. m/z+ion=280.2) The crude reaction product was taken onto the next step without further purification.

Workup

  1. customTo a 100 mL round-bottomed flask equipped
  2. stirringThe reaction mixture was stirred at ambient temperature for 3.5 h
  3. concentrationafter which time the mixture was concentrated in vacuo
  4. additionNaOH (ca. 50 mL of a 1M aq. solution) was added to the mixture
  5. extractionthe aqueous layer was extracted with CH2Cl2 (3×15 mL)
  6. dry with materialdried over K2CO3
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b0bf47b6bcfe4da88d9bba9750dfb671
Source dataset
uspto-grants-2014_04
Patent number
US08686011B2

Reaction notes

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