Aluminium lithium hydride → [3-(2-Methyl-1,3-dioxolan-2-yl)tricyclo[3.3.1.03,7]non-1-yl]methanol

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Reaction Steps

Methyl 3-(2-methyl-1,3-dioxolan-2-yl)tricyclo[3.3.1.03,7]nonane-1-carboxylate (2.3 g, 8.64 mmol) obtained in step III, in THF (15 mL) was added slowly under N2 atmosphere through a dropping funnel to a suspension of LiAlH4 (0.32 g, 8.64 mmol) in ether (15 mL) at ice bath temperature. The reaction mixture was stirred for 30 minutes before being quenched by addition of sat. aq. NH4Cl solution (9 mL), followed by 1N NaOH solution (9 mL) and the reaction mixture was stirred at room temperature for 15 minutes before it was filtered through a pad of celite. The organic layer was washed with brine, dried over Na2SO4 and the solvent was evaporated under reduced pressure to obtain [3-(2-Methyl-1,3-dioxolan-2-yl)tricyclo[3.3.1.03,7]non-1-yl]methanol (1.9 g) in 94% yield as viscous liquid. m/z (M+1) 269; IR cm−1 3436, 2936, 1634, 1459, 1373, 1309, 1047, 757. 1H NMR (CDCl3) 300 MHz δ 4.15-3.80 (m, 4H), 3.53 (s 3H), 2.50-2.30 (m 2H), 1.90-1.30 (m, 10H), 1.29 (s, 3H).

Provenance & Evidence