Ammonium formate → tert-Butyl 2-(pyridin-2-yl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

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Reaction Conditions

Reaction Steps

To tert-butyl 8-benzyl-10-(2-pyridyl)-11-oxa-3,8-diazaspiro[5.5]undec-9-ene-3-carboxylate (80 mg, 0.19 mmol) in methanol (13 mL) was added Pd(OH)2 (50 mg, 0.36 mmol) and ammonium formate (180 mg, 2.85 mmol) and the reaction mixture was heated at 70° C. for 1 hour. The reaction mixture was cooled, diluted with ethyl acetate and filtered through Celite®. The organic layer was washed with 1:1 NaOH:NaHCO3 solution, dried over Na2SO4, filtered and concentrated in vacuo to yield tert-butyl 10-(2-pyridyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (63 mg, 100%) as an oil which was used in the next step without further purification. ESI-MS m/z calc. 333.4. found 334.4 (M+1)+; Retention time: 1.00 minutes (3 min run).

Provenance & Evidence