Dimethylformamide → 1-BOC-4-CHLORO-5-FORMYL-3,6-DIHYDRO-2H-PYRIDINE

HRID 573193Notes

Reaction equation

HRID 573193 reaction equation
CN(C)[CH:3]=[O:4].O=P(Cl)(Cl)[Cl:8].O=[C:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1>ClCCl>[Cl:8][C:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][C:13]=1[CH:3]=[O:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 118450841-BOC-4-CHLORO-5-FORMYL-3,6-DIHYDRO-2H-PYRIDINE

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To N,N-dimethylformamide (3.87 mL) at 0° C., POCl3 (3.73 mL) was added dropwise, maintaining the temperature below 5° C. The resulting mixture was stirred at room temperature for 1.5 hours. The reaction mixture was then cooled in ice bath. Tert-butyl 4-oxopiperidine-1-carboxylate (4.98 g) was added slowly, as a solution in dichloromethane (20 mL). After the addition was complete, the ice bath was removed and the reaction was stirred at room temperature for 1 hour. The reaction mixture was poured over ice and solid sodium acetate, and stirred for 15 minutes, then extracted with dichloromethane. The extracts were washed thoroughly with water and with brine, and dried over MgSO4, filtered, and concentrated under vacuum to obtain the title compound, and used without further purification.

Workup

  1. temperaturemaintaining the temperature below 5° C
  2. temperatureThe reaction mixture was then cooled in ice bath
  3. additionAfter the addition
  4. customthe ice bath was removed
  5. stirringthe reaction was stirred at room temperature for 1 hour
  6. additionThe reaction mixture was poured over ice and solid sodium acetate
  7. stirringstirred for 15 minutes
  8. extractionextracted with dichloromethane
  9. washThe extracts were washed thoroughly with water and with brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-05f1dc8a3002447cbf73fb249c809fd6
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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