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

HRID 712972Notes

Reaction equation

C([N:8]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[O:23][C:10]2([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[N:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH:24]1[O:23][C:10]2([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:12][CH2:11]2)[CH2:9][NH:8][CH2:25]1

Participants

Conditions

Temperature: 70 °C

Procedure

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).

Workup

temperatureThe reaction mixture was cooled
filtrationfiltered through Celite®
washThe organic layer was washed with 1:1 NaOH
dry with materialNaHCO3 solution, dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5c0db311699a4c669a34715221909a2b
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181273B2

Reaction notes

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