[CH2:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:10])[CH2:2][CH3:3].C([N-]C(C)C)(C)C.[Li+].[Br:19][C:20]1[C:21](=O)[CH2:22][CH2:23][CH2:24][C:25]=1[O:26]C>C1C=CC=CC=1.C1COCC1>[Br:19][C:20]1[C:25](=[O:26])[CH2:24][CH2:23][CH2:22][C:21]=1[CH:6]1[CH2:7][CH2:8][CH2:9][N:4]([CH2:1][CH2:2][CH3:3])[C:5]1=[O:10]A solution of 1-propyl-2-piperidone (50 mM) in benzene (40 ml) was added dropwise to a solution of lithium di-isopropylamide [ex n-butyl lithium in hexane (32.3 ml, 50 mM), di-isopropylamine (7 ml, 50 mM) and THF (33 ml)]. A solution of 2-bromo-3-methoxycyclohex-2-en-1-one (10.25 g, 50 mM) in THF (40 ml) was added, and after 5 minutes the mixture was quenched by pouring on to excess aqueous hydrochloric acid. Ether extraction followed by passage through a short silica pad using ethyl acetate as eluant gave the title compound as a colourless oil (10.75 g).
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