tert-Butoxy bis(dimethylamino)methane → tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

HRID 2227820Notes

Reaction equation

HRID 2227820 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O[CH:20](N(C)C)[N:21]([CH3:23])[CH3:22])(C)(C)C>CN(C)C=O.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11](=[O:14])[C:12](=[CH:20][N:21]([CH3:23])[CH3:22])[CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 53395404tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylateYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (prepared according to the method of Example 101, Step A, 4.0 g, 20.0 mmol) in dimethylformamide (40 mL) was added tert-butoxybis(dimethylamino)methane (4.35 mL, 22 mmol). This mixture was stirred at reflux for 15 h, cooled to room temperature, diluted with water, and extracted with ethyl acetate (5×). The combined organic extracts were washed with water (3×) and brine (1×), dried over sodium sulfate, filtered, and evaporated to give 3.64 g (72%) of the title compound of Example 101, Step B as a brown oil that was sufficiently pure to carry on to the next step. 1H NMR (CDCl3, 400 MHz) δ7.47 (s, 1H), 4.53 (s, 2H), 3.58 (t, 2H), 3.09 (s, 6H), 2.43 (t, 2H), 1.46 (s, 9H); MS (APCI) 255 (MH+).

Workup

  1. temperatureat reflux for 15 h
  2. extractionextracted with ethyl acetate (5×)
  3. washThe combined organic extracts were washed with water (3×) and brine (1×)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-841151cd079a4831971aca97ca0410b4
Source dataset
uspto-grants-2002_07
Patent number
US06414149B1

Reaction notes

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