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

HRID 1875569Notes

Reaction equation

HRID 1875569 reaction equation
C(O[CH:6](N(C)C)[N:7]([CH3:9])[CH3:8])(C)(C)C.[O:13]=[C:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1>>[CH3:6][N:7]([CH:9]=[C:19]1[C:14](=[O:13])[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18]1)[CH3:8]

Participants

3

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)-pyridinecarboxylate

Conditions

Temperature
110 °C

Procedure

To tert-butoxy bis(dimethylamino)methane (20.8 mL) was added tert-butyl 4-oxopiperidine-1-carboxylate (20.0 g) and the resulting mixture was heated at 110° C. for 16 h. After cooling to rt, the mixture was purified by flash chromatography on silica gel using a gradient elution of 5% methanol in methylene chloride to 10% methanol in methylene chloride. Concentration of the combined fractions containing the major product afforded the desired product a (11.8 g) as a dark orange oil which was used in the next step without any further purification.

Workup

  1. temperatureAfter cooling to rt
  2. customthe mixture was purified by flash chromatography on silica gel using
  3. washa gradient elution of 5% methanol in methylene chloride to 10% methanol in methylene chloride
  4. additionConcentration of the combined fractions containing the major product

Sources & evidence

ORD record
ord-9f744e1e0336442882fdcc1cb8320125
Source dataset
uspto-grants-2012_11
Patent number
US08309571B2

Reaction notes

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