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

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).

1. custombefore being quenched by addition of sat. aq. NH4Cl solution (9 mL)
2. stirringthe reaction mixture was stirred at room temperature for 15 minutes before it
3. filtrationwas filtered through a pad of celite
4. washThe organic layer was washed with brine
5. dry with materialdried over Na2SO4
6. customthe solvent was evaporated under reduced pressure

ORD record

ord-6b09a1ce3b3a48b4850c5faa588ff0c3

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07985759B2