Ammonium Chloride → HCID 22020970, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of intermediate (28) (0.031 mol) in THF (50 ml) under nitrogen flow at −78° C., lithium diisopropylamine (0.062 mol, 2 M) was slowly added. The reaction mixture was allowed to warm to 0° C. and was stirred for 1 hour. After cooling again to −78° C., a solution of [(phenylmethoxy)methyl]-oxirane (0.034 mol) in THF (40 ml) was added and the mixture was allowed to warm to room temperature and was stirred for 16 hours. A saturated NH4Cl-solution was added and the mixture was extracted with ethyl acetate. The separated organic layer was dried, filtered and the solvent was evaporated. The residue was purified by short open column chromatography over silica gel (eluent: hexane/ethyl acetate 50/50). The product fractions were collected and the solvent was evaporated, yielding 7.18 g of 1-[(2-chloro-3-pyridinyl)methylamino]-3-(phenylmethoxy)-2-propanol (intermediate 29).

Provenance & Evidence