反应详情

温度

-10 °C

To a stirred suspension of CuI (10.2 g, 54 mmol) in ether (120 mL) at −10° C. was added dropwise MeLi (73 mL, 109 mmol, 1.5 M in ether) ensuring that the temperature remained below −5° C. The resulting solution was stirred at −10° C. for 20 min and a solution of phenylmethyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (Example 113) (5 g, 23 mmol) in ether (50 mL) was added, maintaining the temperature below −2° C. The reaction was stirred at −10° C. for 1 hour after which time it was quenched with water and partitioned with DCM. A standard work up yielded phenylmethyl (trans)-3-hydroxy-4-methyl-1-pyrrolidinecarboxylate, which was purified and subjected to chiral chromatography, producing two enantiopure compounds of undetermined absolute stereochemistry. (Yield of E1=1.55 g, yield of E2=1.58 g).

1. customremained below −5° C
2. temperaturemaintaining the temperature below −2° C
3. stirringThe reaction was stirred at −10° C. for 1 hour after which time it
4. customwas quenched with water
5. custompartitioned with DCM