Trifluoroacetic acid → tert-butyl 4-(2-methoxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 276886Notes

Reaction equation

HRID 276886 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](O)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 226295651-Boc-4-(2-methoxyphenyl)-4-hydroxypiperidine

Product 1

HCID 22629561tert-butyl 4-(2-methoxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylateYield 69.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-t-Butoxycarbonyl-4-hydroxy-4-(2-methoxyphenyl)piperidine (230 mg, 0.75 mmol) was dissolved in methylene chloride (10 ml). Thereto was added trifluoroacetic acid (0.20 ml, 2.6 mmol) and the resulting solution was stirred at a room temperature for 2.5 hours. The reaction solution was washed with saturated sodium bicarbonate aqueous solution and saturated brine in that order and dried with anhydrous sodium sulfate. Then the compound obtained by the evaporation of the solvent under a reduced pressure was separated and purified by a silica gel column chromatography to obtain 150 mg of the aforementioned compound of interest (0.53 mmol, 71% in yield).

Workup

  1. washThe reaction solution was washed with saturated sodium bicarbonate aqueous solution and saturated brine in that order
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThen the compound obtained by the evaporation of the solvent under a reduced pressure
  4. customwas separated
  5. custompurified by a silica gel column chromatography
  6. customto obtain

Sources & evidence

ORD record
ord-33668dde66c5413ab0dfbec8f5ed6ed4
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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