Hydrochloric Acid → Tropane

HRID 567627Notes

Reaction equation

HRID 567627 reaction equation
[CH3:1][N:2]1[C@H:6]2[C:7](C(OC)=O)=[CH:8][CH2:9][C@@H:3]1[CH2:4][CH2:5]2.CC1C=CC=CC=1[Mg]Br.FC(F)(F)C(O)=O.Cl.[NH4+].[OH-]>CCOCC.O>[C@@H:3]12[N:2]([CH3:1])[C@@H:6]([CH2:5][CH2:4]1)[CH2:7][CH2:8][CH2:9]2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 119478(-)-Anhydroecgonine methyl esterHCID 178424303HCID 178424303, compound

Product 1

HCID 637986TropaneYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

The anhydroecgonine methyl ester 1 (leq.) is dissolved in 25 ml of anhydrous ether and then added to 5 eq. of (methylphenyl) magnesium bromide at −40° C. After 3 hours of mechanical stirring, the mixture is cooled to −78° C. and treated drop by drop with a solution of 5 ml of trifluoroacetic acid diluted in 25 ml of anhydrous ether. After one hour's stirring, the mixture is brought to 0° C. and then treated with 70 ml of water and 26 ml of concentrated HCl. The aqueous phase is then treated with NH4OH and extracted with ether (3×40 ml). The different organic phases are collected, washed in brine, dried on Na2SO4 and evaporated to produce compound 2 with a yield of 30%.

Workup

  1. customis brought to 0° C.
  2. extractionextracted with ether (3×40 ml)
  3. customThe different organic phases are collected
  4. washwashed in brine
  5. customdried on Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-bdd6a9fe471449f18dbd61752651b4d0
Source dataset
uspto-grants-2001_01
Patent number
US06180083B2

Reaction notes

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