tert-butyl 4-(4-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate → Pyridine, 1,2,3,6-tetrahydro-4-[4-(trifluoromethyl)phenyl]-

HRID 380479Notes

Reaction equation

HRID 380479 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:23][C:20]([F:21])([F:22])[C:17]1[CH:16]=[CH:15][C:14]([C:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 1

HCID 18364827tert-butyl 4-(4-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 12440708Pyridine, 1,2,3,6-tetrahydro-4-[4-(trifluoromethyl)phenyl]-Yield 2,121.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 0.4 g (0.112 mmol) of 1-t-butoxycarbonyl-4-(4-trifluoromethyl phenyl)-1,2,3,6-tetrahydropyridine in 1 mL of TFA and 3 mL of CH2Cl2 was stirred at rt for 1 h. The reaction mixture was then concentrated. A mixture of the residue and 0.1 g of 10% Pd/C in 20 mL of MeOH was hydrogenated at 45 psi for 4 h. The reaction mixture was flitered though a plug of celite and concentrated to give 0.54 g of the title compound. 1H NMR (CDCl3) δ1.94 (m,2H), 2.06 (m, 2H), 3.00 (m, 1H), 3.11 (m, 2H), 3.49 (m, 2H), 7.45 (d, 2H, J=8 Hz), 7.62 (d, 2H, J=8 Hz)

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additionA mixture of the residue and 0.1 g of 10% Pd/C in 20 mL of MeOH
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f682aa2c31d44e1a9cf8f9632fa2df3d
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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