Pyridine → 6-Chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 1020309Notes

Reaction equation

HRID 1020309 reaction equation
N1C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C(NC(=O)[O-])C.O[C:29]1[C:30]([Cl:42])=[CH:31][C:32]2[CH:33]([CH3:41])[CH:34]3[CH2:38][NH:37][CH2:36][CH:35]3[C:39]=2[CH:40]=1>C(Cl)Cl>[Cl:42][C:30]1[CH:29]=[CH:40][C:39]2[CH:35]3[CH2:36][NH:37][CH2:38][CH:34]3[CH:33]([CH3:41])[C:32]=2[CH:31]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 86602845N-Ethylcarbamate 5-hydroxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Product 1

HCID 116370656-Chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridine (0.23 mL, 2.85 mmol) and trifluoromethanesulfonic anhydride (0.32 mL, 1.90 mmol) were added to a solution of N-ethylcarbamate-5-hydroxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (0.28 g, 0.95 mmol) in CH2Cl2 (10 mL), and stirred for 1.5 hours at room temperature. The reaction was diluted with CH2Cl2 (10 mL), washed with H2O (10 mL), aqueous HCl (1.0 M, 10 mL), saturated aqueous NaHCO3 (10 mL), and brine (10 mL). The organic extract was dried over MgSO4 and concentrated to afford the subtitle compound, which was used without further purification. MS calculated for C16H17F3ClNO5S+H: 428, observed: 428.

Workup

  1. washwashed with H2O (10 mL), aqueous HCl (1.0 M, 10 mL), saturated aqueous NaHCO3 (10 mL), and brine (10 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8998c71d5aa44fc7af3c64db244015ce
Source dataset
uspto-grants-2014_05
Patent number
US08716324B2

Reaction notes

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