1-Methyl-3-pyrrolidinol, (-)- → HCID 86602256, compound

HRID 458890Notes

Reaction equation

HRID 458890 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]([OH:15])([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[C:5]1[S:6][CH:7]=[CH:8][CH:9]=1.[CH3:17][N:18]1[CH2:22]C[C@@H:20](O)[CH2:19]1>C1(C)C=CC=CC=1>[CH3:17][N:18]1[CH2:19][CH2:20][C@@H:1]([O:2][C:3](=[O:16])[C:4]([OH:15])([C:5]2[S:6][CH:7]=[CH:8][CH:9]=2)[C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH2:22]1

Participants

4

Reactant 2

HCID 69513321-Methyl-3-pyrrolidinol, (-)-HCID 11414137Methyl alpha-hydroxy-alpha-2-thienyl-2-thiopheneacetate

Product 1

HCID 86602256HCID 86602256, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

1 g of 2-Hydroxy-2,2-dithien-2-ylacetic acid methyl ester (0.0039 mol) was dissolved in 30 ml of toluene. To this solution were added 0.394 g (0.0039 mol) of (3R)-1-methylpyrrolidin-3-ol (Intermediate I-19), and 0.078 g (0.00195 mol) of HNa (60% dispersion in mineral oil). The mixture was stirred 30 min at room temperature, refluxed for 1 hour, and then refluxed with continuous removal of distillate with replacement with fresh toluene when necessary for 2 hours. The cooled mixture was extracted with 2N HCl, the aqueous layer was washed with a small volume of ethyl acetate, basified with solid K2CO3 and extracted three times with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and evaporated. The yield was 0.73 g (58%) of the title product (structure confirmed by 1H-NMR). This product was purified by chromatography on silica gel eluting with chloroform/ethanol/NH4OH (200:8:1). Appropriate fractions were combined and evaporated to give the title compound.

Workup

  1. temperaturerefluxed for 1 hour
  2. extractionThe cooled mixture was extracted with 2N HCl
  3. washthe aqueous layer was washed with a small volume of ethyl acetate
  4. extractionextracted three times with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThis product was purified by chromatography on silica gel eluting with chloroform/ethanol/NH4OH (200:8:1)
  9. customevaporated

Sources & evidence

ORD record
ord-6454d1074e40479db8fb778b6feb89b0
Source dataset
uspto-grants-2007_03
Patent number
US07192978B2

Reaction notes

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