Dimethylformamide → 8-Ethoxycarbonyl-3-chloro-2-formyl-8-azabicyclo[3.2.1]oct-2-ene

HRID 649793Notes

Reaction equation

HRID 649793 reaction equation
CN([CH:4]=[O:5])C.O=P(Cl)(Cl)[Cl:8].[CH2:11]([O:13][C:14]([N:16]1[CH:21]2[CH2:22][CH2:23][CH:17]1[CH2:18][C:19](=O)[CH2:20]2)=[O:15])[CH3:12]>C(Cl)Cl>[CH2:11]([O:13][C:14]([N:16]1[CH:21]2[CH2:22][CH2:23][CH:17]1[C:18]([CH:4]=[O:5])=[C:19]([Cl:8])[CH2:20]2)=[O:15])[CH3:12]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 401882Ethyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylate

Product 1

HCID 217086698-Ethoxycarbonyl-3-chloro-2-formyl-8-azabicyclo[3.2.1]oct-2-eneYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of dry DMF (45 g, 0.6 mol) in dry CH2Cl2 (150 ml) was added POCl3 (75 g, 0.5 mol) at 0-10° C. 8-Ethoxycarbonyl-8-azabicyclo[3.2.1]octane-3-one (57 g, 0.29 mol) dissolved in dry CH2Cl2 (60 ml) was added. The reaction mixture was stirred over night at room temperature, then added to ice water (1.000 ml). The phases were separated and the water phase extracted with CH2Cl2 (2×200 ml). The combined CH2Cl2 extracts were washed with a saturated NaHCO3 solution and water, dried and evaporated to give 70 g of the title compound, which was used in the next step without further purification.

Workup

  1. additionwas added
  2. customThe phases were separated
  3. extractionthe water phase extracted with CH2Cl2 (2×200 ml)
  4. washThe combined CH2Cl2 extracts were washed with a saturated NaHCO3 solution and water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-ffc3ecaa66044f51ac7e3f6daa4d70d1
Source dataset
uspto-grants-2001_08
Patent number
US06271229B1

Reaction notes

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