Triethylamine → 1-Tert-butyl 3-methyl 1,2,5,6-tetrahydropyridine-1,3-dicarboxylate

HRID 2115675Notes

Reaction equation

HRID 2115675 reaction equation
O[CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH:3]1[C:15]([O:17][CH3:18])=[O:16].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>CN(C)C1C=CN=CC=1.ClCCl>[N:5]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7][CH:2]=[C:3]([C:15]([O:17][CH3:18])=[O:16])[CH2:4]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 185348061-Tert-butyl 3-methyl 4-hydroxypiperidine-1,3-dicarboxylate

Product 1

HCID 111284441-Tert-butyl 3-methyl 1,2,5,6-tetrahydropyridine-1,3-dicarboxylateYield 46%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) solution of 1-tert-butyl 3-methyl 4-hydroxy-1,3-piperidinedicarboxylate (1,64 g, 6.32 mmol), 4-dimethylaminopyridine (16.0 mg, 0.13 mmol), and triethylamine (2.64 mL, 19.0 mmol) in dichloromethane (25 mL) was added dropwise trifluoroacetic anhydride (1.12 mL, 7.91 mmol). The reaction mixture was stirred at room temperature for 40 hrs. The reaction was quenched with 10% K2CO3 solurtion, extracted with CHCl3. The separated organic phase was washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give 1-tert-butyl 3-methyl 5,6-dihydro-1,3(2H)-pyridinedicarboxylate as a pale yellow oil. (707.4 mg, yield 46%)

Workup

  1. customThe reaction was quenched with 10% K2CO3 solurtion
  2. extractionextracted with CHCl3
  3. washThe separated organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-7c8575cbb408419bb82ffd8173e230cd
Source dataset
uspto-grants-2008_10
Patent number
US07435743B2

Reaction notes

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