Trifluoromethanesulfonic acid → HCID 71118335, compound

HRID 2045793Notes

Reaction equation

HRID 2045793 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=[O:15])[C@@H:13]3[C@H:9]2[CH2:10][CH2:11][CH2:12]3)=[CH:4][CH:3]=1.OS(C(F)(F)F)(=O)=O>ClC(Cl)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][CH:9]3[CH2:10][CH2:11][CH2:12][CH:13]3[C:14](=[O:15])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 71117334HCID 71117334, compound

Product 1

HCID 71118335HCID 71118335, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

A 500-mL, three-necked, round-bottomed flask was charged with cis-6-(4-fluorophenyl)-6-azabicyclo[3.2.0]heptan-7-one (racemic 17DP) (26.5 g, 129 mmol) and 250 mL of dichloroethane. The reaction mixture was cooled at 5° C. while triflic acid was added via syringe over 10 min. The reaction mixture was stirred at 50° C. for 4 h. The reaction mixture was cooled to room temperature with an ice-water bath and then quenched with saturated sodium bicarbonate to adjust the pH to 10. The organic layer was separated, washed with brine, dried over MgSO4, filtered, and concentrated to give 26.5 g of a 90:10 mixture of the title compound as a brown semi-solid.

Workup

  1. additionwas added via syringe over 10 min
  2. temperatureThe reaction mixture was cooled to room temperature with an ice-water bath
  3. customquenched with saturated sodium bicarbonate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give

Sources & evidence

ORD record
ord-7e5f96a1be0844298d4f7a0db5d42bf5
Source dataset
uspto-grants-2013_11
Patent number
US08592383B2

Reaction notes

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