Lithium diisopropylamide → Ethyl 1-azabicyclo(2.2.2)octane-4-carboxylate

A solution of ethyl 1-(2-chloroethyl)-4-piperidinecarboxylate (20.42 g, 92.9 mmol) in THF (600 mL) was cooled to −50° C. under Ar. LDA (2.0 M in heptane/THF/ethyl benzene, 70 mL, 140 mmol) was slowly added to the solution at −50° C. over 25 min. The reaction was allowed to warm up to room temperature over 16 h. The reaction was quenched with K2CO3 (saturated aqueous) (500 mL) and extracted with Et2O (3×500 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under vacuum. The resulting orange oil was co-evaporated three times with DCM to remove excess ethyl benzene, resulting in the title compound (16.29 g, 95.7%). EI-MS m/z 184(M+H+) Rt (1.08 min).

1. customThe reaction was quenched with K2CO3 (saturated aqueous) (500 mL)
2. extractionextracted with Et2O (3×500 mL)
3. dry with materialThe combined organic layers were dried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated under vacuum
6. customto remove excess ethyl benzene

ORD-Eintrag

ord-76a37454e8034072be96957a325b7d0d

Quelldatensatz

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07498440B2