m-Fluorobenzenethiol → HCID 59207197, compound

Participants

Reaction Steps

In 5 mL dioxane under argon was mixed 1-((R)-6-Iodo-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-azetidin-3-ol (0.172 g, 0.5 mmol), tris(dibenzylideneacetone)-dipalladium(0) (0.023 g, 0.025 mmoles), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.029 g, 0.05 mmol), diisopropylethyl amine (1 mmol) and 3-fluoro-thiophenol (0.13 g, 1.0 mmoles). The reaction mixture was stirred at 60° for 45 minutes, then was cooled and diluted with EtOAc. The organic layer was washed 1.5 M aqueous sodium carbonate, dried (magnesium sulfate), filtered and concentrated under reduced pressure. The residue was subjected to preparative HPLC (hexanes/EtOAc 1:1 to 50% hexanes/27% EtOA/15% MeOH/8% con. NH4OH) to give 0.08 g (47%) of 1-[(R)-6-(3-fluoro-phenylsulfanyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-azetidin-3-ol, MS M+H=344.

Provenance & Evidence