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

HRID 1611150Notes

Reaction equation

HRID 1611150 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 solution, 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 solution
  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-d46e6d4c086e4897abd5d6ffe8a2bcf3
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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