Sodium Methoxide → HCID 68470880, compound

HRID 1598011Notes

Reaction equation

HRID 1598011 reaction equation
[C:1]([C@H:5]1[C@@H:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10][C@H:9]2[N:19]([CH3:20])[C@@H:6]1[CH2:7][CH2:8]2)([O:3][CH3:4])=[O:2].C[O-].[Na+]>CO>[C:1]([C@@H:5]1[C@@H:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10][C@H:9]2[N:19]([CH3:20])[C@@H:6]1[CH2:7][CH2:8]2)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 70047392HCID 70047392, compound

Product 1

HCID 68470880HCID 68470880, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (1R,2S,3S)-2-carbomethoxy-3-benzyltropane (5.6 g, 20.5 mmol) in absolute methanol (100 ml) was added a solution of sodium methanolate in methanol (2M, 2 ml) and the mixture was refluxed for 16 hours. The reaction mixture was concentrated in vacuo and the residue was dissolved in diethyl ether and was washed with water. The organic phase was dried and concentrated in vacuo. The crude product was purified by column chromatography using a mixture of diethyl ether and pentane (1+1)+1% triethyl amine as eluent yielding (1R,2R,3S)-2-carbomethoxy-3-benzyltropane as oil. By dissolution of this product in diethyl ether and subsequent addition of a solution of hydrochloric acid in diethyl ether the title compound precipitated as white crystals, m.p. 188°-190° C.

Workup

  1. temperaturethe mixture was refluxed for 16 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in diethyl ether
  4. washwas washed with water
  5. customThe organic phase was dried
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography
  8. additiona mixture of diethyl ether and pentane (1+1)+1% triethyl amine as eluent

Sources & evidence

ORD record
ord-0194a635d3e640819b716ff73b20c0fd
Source dataset
uspto-grants-1998_04
Patent number
US05736556

Reaction notes

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