Hexane → HCID 67364898, compound

Participants

Reaction Steps

To a stirred solution of (RS)-1-(2-bromo-phenyl)-ethanol (8.0 g, 39.8 mmol) −70° C. in tetrahydrofuran (40 ml) was added dropwise a 1.6M n-butyllithium solution in hexane (57.2 ml, 91.5 mmol) over a period of 20 min. After 2 hours, a solution of 1-benzyl-4-piperidone (10.2 ml, 55.7 mmol) in tetrahydrofuran (32 ml) was added dropwise. The mixture was allowed to warm to room temperature and stirred overnight. The mixture was poured into a stirred mixture of water (200 ml) and ether (200 ml). The aqueous layer was extracted with ether (2×100 ml). The combined extracts were washed with water (80 ml), dried over Na2SO4, filtered and concentrated in vacuo. The crude oil was chromatographed on silica gel (eluent: heptane/ethylacetate 3:7) to yield 6.1 g (49%) of (RS)-1-benzyl-4-[2-(1-hydroxy-ethyl)-phenyl]-piperidin-4-ol as a white solid. MS m/e: 312 (M+H+).

Provenance & Evidence