Hydrochloric Acid → HCID 9822797, compound

Participants

Reaction Steps

tert-Butyl 1-acetoxy-6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1H-pyrrolizin-5-ylacetate (example 9c, 1.00 g, 2.0 mmol) is dissolved in 10 ml of MeOH. 0.5 g of KOH is added and the mixture is heated under reflux until the intermediately formed precipitate has dissolved. It is then allowed to cool and is stirred into 600 ml of water. The cloudy solution is brought to pH 3 using conc. HCl. It is extracted three times using 100 ml of diethyl ether each time. The ether extracts are washed twice with water and dried over Na2SO4, filtered and concentrated in a rotary evaporator. A mixture of 6-(4-chlorophenyl)-2,3-dihydro-1-hydroxy-2,2-dimethyl-7-phenyl-1H-pyrrolizin-5-ylacetic acid and 2-[6-(4-chlorophenyl)-2,3-dihydro-1-methoxy-2,2-dimethyl -7-phenyl-1H-pyrrolizin-5-yl]acetic acid is obtained (cf. example 16).

Provenance & Evidence