[CH2:1]1[C:3]2([CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]2)[CH2:2]1.Cl.[CH3:11][NH:12][CH3:13].Cl.[C:15]([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:11][N:12]([CH2:15][CH:7]1[C:6](=[O:9])[CH2:5][CH2:4][C:3]2([CH2:2][CH2:1]2)[CH2:8]1)[CH3:13]
Stir a mixture of spiro[2.5]octan-6-one (252 mg, 2.03 mmol), (HCHO)n (61 mg, 2.03 mmol), dimethylamine hydrochloride (166 mg, 2.03 mmol) and 0.3 mL of conc. HCl in MeCN (30 mL) at 60° C. for 6 hours. Quench the reaction with saturated aqueous NH4Cl solution (15 mL). Basify the aqueous solution with K2CO3 to pH=9. Extract the aqueous mixture with EtOAc (30 mL×2). The combined organic layers are washed with brine (15 mL), dried over Na2SO4, filtered, and concentrated under vacuum. Purify the residue by silica gel chromatography (CH2Cl2:MeOH=30:1) to afford 5-Dimethylaminomethyl-spiro[2.5]octan-6-one as brown oil (142 mg, yield: 38.4%). MS (m/z): 182 (M+1).
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