Trifluoroacetic acid → benzyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 385815Notes

Reaction equation

HRID 385815 reaction equation
[F:1][C:2]([F:21])([F:20])[S:3]([O:6][C:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])(C)C)=[O:14])[CH2:9][CH:8]=1)(=[O:5])=[O:4].FC(F)(F)C(O)=O.C(N(CC)CC)C.ClC(OC[C:41]1[CH:46]=[CH:45]C=[CH:43][CH:42]=1)=O>ClCCl>[F:21][C:2]([F:1])([F:20])[S:3]([O:6][C:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:19]2[CH:45]=[CH:46][CH:41]=[CH:42][CH:43]=2)=[O:14])[CH2:9][CH:8]=1)(=[O:4])=[O:5]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 11303044benzyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 50 mL roundbottom flask, was placed tert-butyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (3.5 g, 10.00 mmol). To this was added dichloromethane (20 mL) followed by the addition of trifluoroacetic acid (5 mL). The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at room temperature. The mixture was concentrated by evaporation under vacuum using a rotary evaporator. This was followed by the addition of dichloromethane (20 mL). This was followed by the addition of triethylamine (3.03 g, 29.94 mmol). To the mixture was added benzyl chloroformate (2.05 g, 12.02 mmol). The resulting solution was allowed to react overnight at room temperature. The reaction mixture was filtered and the filtrate was concentrated under vacuo. The crude mixture was purified by silica gel chromatography (1:40 EtOAc/petroleum ether) to yield the title compound as a yellow liquid.

Workup

  1. customInto a 50 mL roundbottom flask, was placed
  2. customto react
  3. concentrationThe mixture was concentrated by evaporation under vacuum
  4. customa rotary evaporator
  5. additionThis was followed by the addition of dichloromethane (20 mL)
  6. customto react overnight at room temperature
  7. filtrationThe reaction mixture was filtered
  8. concentrationthe filtrate was concentrated under vacuo
  9. customThe crude mixture was purified by silica gel chromatography (1:40 EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-2a32d75af77741d8a5880a5a4860d506
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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