(1α,2β,4β,5α)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7α-ol → Scopine-2,2-dithienyl glycolate

HRID 914636Notes

Reaction equation

HRID 914636 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)([OH:11])[C:7]([O:9][CH3:10])=[O:8].[CH3:17][N:18]1[C@@H:23]2[C@@H:24]3[O:26][C@@H:25]3[C@H:19]1[CH2:20]C(O)[CH2:22]2.[Na]>C1(C)C=CC=CC=1>[CH3:17][N:18]1[C@@H:23]2[C@@H:24]3[O:26][C@@H:25]3[C@H:19]1[CH2:20][CH:10]([O:9][C:7]([C:6]([OH:11])([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)=[O:8])[CH2:22]2

Participants

5

Reactant 3

HCID 1274465(1α,2β,4β,5α)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7α-olHCID 5360545SodiumHCID 11414137Methyl alpha-hydroxy-alpha-2-thienyl-2-thiopheneacetate

Product 1

HCID 29927228Scopine-2,2-dithienyl glycolate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

50.87 g (0.2 mole) of methyl di-(2-thienyl)glycolate and 31.04 g (0.2 mole) of scopine are dissolved in 100 ml of absolute toluene and reacted at a bath temperature of 90° C. with addition of 1.65 g (0.071 gram atom) of sodium in several portions. The resulting methanol is distilled off at a reaction mixture temperature of 78°-90° C. under a pressure of 500 mbar. After a reaction time of about 5 hours, the reaction mixture is stirred into a mixture of ice and hydrochloric acid. The acid phase is separated off, rendered alkaline using sodium carbonate and the free base is extracted using methylene chloride. After drying over sodium sulphate, the methylene chloride is distilled off under reduced pressure and the residue is recrystallised from acetonitrile; beige-coloured crystals (from acetonitrile).

Workup

  1. customreacted at a bath temperature of 90° C.
  2. distillationThe resulting methanol is distilled off at a reaction mixture temperature of 78°-90° C. under a pressure of 500 mbar
  3. customThe acid phase is separated off
  4. extractionthe free base is extracted
  5. dry with materialAfter drying over sodium sulphate
  6. distillationthe methylene chloride is distilled off under reduced pressure
  7. customthe residue is recrystallised from acetonitrile

Sources & evidence

ORD record
ord-1651ebeb2c6e49e48cba76c2cc3a76b4
Source dataset
uspto-grants-2007_09
Patent number
USRE039820E1

Reaction notes

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