Sodium Methoxide → HCID 68470880, compound

HRID 742315Notes

Reaction equation

HRID 742315 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 remanescens 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 an oil. By dissolution of this product in diethyl ether and subsequent addition of a solution of hydrochloric acid in diethyl ether the title compound precipitates 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 remanescens 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-08367a9b40a745909e747f12ad2c1b2f
Source dataset
uspto-grants-1996_09
Patent number
US05554626

Reaction notes

Loading…