[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11]C(OC)=O)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH3:16][Mg]I.[Cl-].[NH4+].Cl.CC[O:24][CH2:25][CH3:26]>>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][C:25]([CH3:26])([CH3:16])[OH:24])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]Crude methyl 3-(1-acetyl-piperid-4-yl)propionate (13 g) in dry ether (80 ml) was added dropwise, at 0°-10°, to methyl magnesium iodide [prepared from Mg (8 g) and methyliodide (40 g)] in dry ether (150 ml). The mixture was then stirred at room temperature (20°) overnight, after which time the resulting complex was decomposed by the addition of saturated, aqueous ammonium chloride (50 ml). Dilute hydrochloric acid was added until all the solids dissolved (pH 7-8) and then the ether layer was separated. The aqueous layer was extracted with ether (200 ml) and chloroform (200 ml) and the combined organic extracts were washed with 2 N hydrochloric acid (100 ml) and then with brine (50 ml). After drying (Na2CO3), the organic solvents were removed in vacuo to give 3-(1-acetyl-piperid-4-yl)-1,1-dimethyl propanol as a crude oil.
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