(3-endo)-benzyl3-(hydroxymethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate synthesis

Yield:1067230-68-5 61%

Reaction Conditions:

with triethylamine in acetonitrile at 0 - 20; for 2 h;

Steps:

29.4

TEA (4.4 mL, 31.65 mmol) was added to a suspension of 100a (2.98 g, 21.103 mmol) in MeCN (70 mL) and the reaction flask was cooled to 0° C. Benzyl chloroformate (4.8 mL, 31.65 mmol) was added to the solution and the reaction mix was allowed to warm up to RT and stirred for 2 h. The residue was partitioned between water and DCM and the aqueous layer was back extracted twice with DCM. The combined extract were dried (Na₂SO₄), filtered and evaporated. The remaining orange oil was purified by SiO₂ chromatography eluting with a MeOH/DCM gradient (0 to 4% MeOH) to afford 3.57 g (61%) of 100b as a light yellow oil.

References:

US2008/249087,2008,A1 Location in patent:Page/Page column 33