Nitrogen → HCID 131717470, compound

Participants

Reaction Steps

To a solution of crude trans-2-(4-ethoxy-3-methoxy-5-n-propylthiophenyl)-5-(3,4,5-trimethoxyphenyl)cyclopentanone (6.87 g, 14.5 mmoles) in MeOH (230 ml) was added at room temperature NaBH4 (1.64 g, 43.4 mmoles) in several portions over 5 minutes. The solution was stirred at room temperature in a N2 atmosphere for 21 hours and most of the MeOH removed in vacuo. The residue was suspended in H2O and extracted with Et2O (4×). The combined extracts were washed with H2O (3×) and saturated NaCl solution and dried (MgSO4). The residue after evaporation of the Et2O in vacuo was filtered through a 9.5×11 cm column of silica gel (E. Merck, Kriselgel 60 ) with (1:1) EtOAc-hexane (21). Evaporation in vacuo gave 6.12 g of a crude mixture of cyclopentanols. Separation by HPLC on a Prep 500 with silica gel and 2:1 hexane-EtOAc gave 2.27 g (33 % from 1) of 1β, 2β, 5α)-2-(4-ethoxy-3-methoxy-5-n-propylthiophenyl)-5-(3,4,5-trimethoxyphenyl)cyclopentanol (5, eluted first).

Provenance & Evidence