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0 °C

To an ice cooled solution of 9-(3,4-dichloro-phenyl)-3-aza-spiro[5.5]undec-8-ene (410 mg, 1.38 mmol) in dichloroethane (12 mL) and methanol (4 mL), formaldehyde (37% in water, 157 μL, 2.08 mmol) was added and stirred for 1 h at 0° C. Sodium triacetoxy-borohydride (585 mg, 2.76 mmol) was added and the mixture stirred at room temperature over night. The reaction was quenched with aqueous sodium hydrogen-carbonate and evaporated. The remaining aqueous phase was extracted four times with dichloromethane and the combined organic phase was dried (sodium sulfate), filtered and evaporated to give 320 mg of crude material. Flash chromatography (dichloromethane/methanol 9:1 with 1% ammonium hydroxide) gave 225 mg (52%) of 9-(3,4-dichloro-phenyl)-3-methyl-3-aza-spiro[5.5]undec-8-ene as an yellow oil.

1. stirringthe mixture stirred at room temperature over night
2. customThe reaction was quenched with aqueous sodium hydrogen-carbonate
3. customevaporated
4. extractionThe remaining aqueous phase was extracted four times with dichloromethane
5. dry with materialthe combined organic phase was dried (sodium sulfate)
6. filtrationfiltered
7. customevaporated
8. customto give 320 mg of crude material