Potassium Carbonate → Ecgonine methyl ester

HRID 462023Notes

Reaction equation

HRID 462023 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]1[C@H:12]2[C@@H:13]([C:17]([O:19][CH3:20])=[O:18])[C@@H:14]([OH:16])[CH2:15][C@@H:9]1[CH2:10][CH2:11]2.Cl>O>[CH3:7][N:8]1[C@H:12]2[C@@H:13]([C:17]([O:19][CH3:20])=[O:18])[C@@H:14]([OH:16])[CH2:15][C@@H:9]1[CH2:10][CH2:11]2

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 162352Methyl 3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 104904Ecgonine methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 20ml of cold saturated potassium carbonate solution in a 125ml separator funnel was added a solution of 5.0g (213 mmoles) ecgonine methyl ester hydrochloride in 5ml water. The aqueous mixture was extracted with 4 × 60ml of chloroform. The combined chloroform extracts were dried over anhydrous sodium carbonate and evaporated in vacuo. Pumping at 0.05mm Hg for 15 minutes yielded 4.0g (93%) of TLC pure (20:1 CHCl3 :MeOH) ecgonine methyl ester.

Workup

  1. extractionThe aqueous mixture was extracted with 4 × 60ml of chloroform
  2. dry with materialThe combined chloroform extracts were dried over anhydrous sodium carbonate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-dccdcd55bc5745b6ac1e8035060defa0
Source dataset
uspto-grants-1977_12
Patent number
US04065354

Reaction notes

Loading…