Carbon Dioxide → 8-ethyl-8-azabicyclo[3.2.1]octan-3-one

HRID 648192Notes

Reaction equation

HRID 648192 reaction equation
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)[O:4]1.Cl.C(C(O)=O)[C:12]([CH2:14][C:15](O)=O)=O.C([O-])(=O)CC(CC([O-])=O)(C([O-])=O)O.[Na+].[Na+].[Na+].[CH2:37]([NH2:39])[CH3:38].C(=O)=O>O>[CH2:37]([N:39]1[CH:6]2[CH2:5][CH2:12][CH:14]1[CH2:15][C:3](=[O:4])[CH2:7]2)[CH3:38]

Participants

8

Reactant 6

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 6224Trisodium citrateHCID 6341EthylamineHCID 68328Acetonedicarboxylic acidHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 2729578-ethyl-8-azabicyclo[3.2.1]octan-3-oneYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

52 ml of 2,5-dimethoxy-tetrahydrofuran (0.402 moles) are dissolved in 58 ml of water and acidified with 1.2 ml of 37% hydrochloric acid. After 15 minutes, 58 g of acetonedicarboxylic acid (0.397 moles) are added followed by 40.4 g of tribasic sodium citrate bihydrate (0.137 moles) dissolved in 58 ml of water. 18.5 g of ethylamine (0.411 moles) in 35 ml of water are then dripped in. The mixture is left stirring until carbon dioxide ceases to be evolved. It is then saturated with K2CO3 and extracted with ethyl ether. After drying and evaporating the solvent, the crude product is distilled under vacuum. 27.9 g of 8-ethyl-8-azabicyclo-[3.2.1]-octan-3-one are obtained.

Workup

  1. waitThe mixture is left
  2. extractionsaturated with K2CO3 and extracted with ethyl ether
  3. customAfter drying
  4. customevaporating the solvent
  5. distillationthe crude product is distilled under vacuum

Sources & evidence

ORD record
ord-d7fc5ef1874843058f1260b1529652ea
Source dataset
uspto-grants-1983_10
Patent number
US04411902

Reaction notes

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