Water → trifluoro-methanesulfonic acid cis-1-(2,2,2-trifluoro-acetyl)-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridin-6-yl ester

HRID 455363Notes

Reaction equation

HRID 455363 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[F:16][C:17]([F:35])([F:34])[C:18]([N:20]1[CH2:25][CH2:24][CH2:23][C@@H:22]2[C:26]3[CH:27]=[C:28](O)[CH:29]=[CH:30][C:31]=3[CH2:32][C@H:21]12)=[O:19].C(N(CC)CC)C.O>CN(C)C1C=CN=CC=1.ClCCl>[F:35][C:17]([F:16])([F:34])[C:18]([N:20]1[CH2:25][CH2:24][CH2:23][C@@H:22]2[C:26]3[CH:27]=[C:28]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])[CH:29]=[CH:30][C:31]=3[CH2:32][C@H:21]12)=[O:19]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 582944732,2,2-Trifluoro-1-(cis-6-hydroxy-2,3,4,4a,9,9a-hexahydro-indeno[2,1-b]pyridin-1-yl)-ethanone

Product 1

HCID 58294405trifluoro-methanesulfonic acid cis-1-(2,2,2-trifluoro-acetyl)-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridin-6-yl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Trifluoromethanesulfonic anhydride (5.6 mL) is added dropwise to a solution of 2,2,2-trifluoro-1-(cis-6-hydroxy-2,3,4,4a,9,9a-hexahydro-indeno[2,1-b]pyridin-1-yl)-ethanone (7.3 g), triethylamine (7.2 mL), and 4-dimethylaminopyridine (50 mg) in dichloromethane (60 mL) chilled in an ice bath. The solution is stirred with cooling for 1 h and at room temperature for 2 h. Water (100 mL) and dichloromethane (100 mL) are then added and the organic phase is separated. The organic phase is washed with water (50 mL), dried (MgSO4), and concentrated to give the title compound as a dark oil. Yield: 10.7 g (quantitative); TLC: rf=0.50 (silica gel, cyclohexane/ethyl acetate 3:1); Mass spectrum (ESI+): m/z=418 [M+H]+.

Workup

  1. temperaturechilled in an ice bath
  2. customthe organic phase is separated
  3. washThe organic phase is washed with water (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9709042c1cea4aa9b73ce67a70595477
Source dataset
uspto-grants-2013_07
Patent number
US08497281B2

Reaction notes

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