Formaldehyde → 9-(3,4-Dichlorophenoxy)-3-methyl-3-azaspiro[5.5]undecane

Participants

Reaction Conditions

Reaction Steps

To a ice cooled solution of 9-(3,4-dichloro-phenoxy)-3-aza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester (60 mg, 0.19 mmol) in dichloroethane (10 mL), formaldehyde (37% in water, 54 μL, 0.72 mmol) was added and stirred for 1 h at 0° C. Sodium triacetoxyborohydride (102 mg, 0.48 mmol) was added and stirred over night at room temperature. 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 75 mg (95%) 9-(3,4-dichloro-phenoxy)-3-methyl-3-aza-spiro[5.5]undecane as a yellow oil. LC-ESI-HRMS of [M+H]+ shows 328.1249 Da. Calc. 328.123495 Da, dev. 4.3 ppm.

Provenance & Evidence