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

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Reaction Steps

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.

Provenance & Evidence