Potassium Carbonate → Ecgonine methyl ester

HRID 1658945Notes

Reaction equation

HRID 1658945 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 20 ml of cold saturated potassium carbonate solution in a 125 ml separatory funnel was added a solution of 5.0 g (213 mmoles) ecgonine methyl ester hydrochloride in 5 ml water. The aqueous mixture was extracted with 4 × 50 ml of chloroform. The combined chloroform extracts were dried over anhydrous sodium carbonate and evaporated in vacuo. Pumping at 0.05 mm Hg for 15 minutes yielded 4.0 g (93%) of TLC pure (20:1, CHCl3 :MeOH) ecgonine methyl ester.

Workup

  1. extractionThe aqueous mixture was extracted with 4 × 50 ml of chloroform
  2. dry with materialThe combined chloroform extracts were dried over anhydrous sodium carbonate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-9a9309b4f8f840eb93ea22472d51e604
Source dataset
uspto-grants-1976_06
Patent number
US03966764

Reaction notes

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