Aluminium lithium hydride → (3R,6S)-6-benzhydryl-tetrahydropyran-3-ol

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Reaction Steps

(1S,4S,6R)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]-heptane 28a (0.3 g, 1.13 mmol) in dry pentane (10 ml) was added to a suspension of LiAlH4 (0.21 g, 5.64 mmol) in dry pentane (20 ml). The resulting reaction mixture was stirred under N2 for 20 hr at room temperature, and then quenched with 10% NaOH, diluted with ethyl acetate (30 ml), and the precipitate removed by filtration. The organic phase was washed with brine and dried over anhydrous Na2SO4. Removal of solvent followed by flash chromatography of the crude product produced pure (3R,6S)-6-benzhydryl-tetrahydro-pyran-3-ol, 33a, 0.23 g (75%, [α]D=(−)-61.6, c=1, MeOH).

Provenance & Evidence