Ammonium formate → Tert-butyl 9-phenyl-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate

HRID 712977Notes

Reaction equation

COC1C=CC(C[N:10]2[CH:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:26][O:25][C:12]3([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[CH2:11]2)=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[C:28]1([CH:27]2[CH2:26][O:25][C:12]3([CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:16][CH2:17]3)[CH2:11][NH:10]2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To tert-butyl 8-[(4-methoxyphenyl)methyl]-9-phenyl-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (500 mg, 1.11 mmol), Pd (500 mg, 4.70 mmol) and ammonium formate (697 mg, 11.05 mmol) was added methanol. The reaction mixture was then heated at 70° C. for 16 hours. The reaction mixture was filtered through a plug of celite and the solvent was concentrated in vacuo to obtain tert-butyl 9-phenyl-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (340 mg, 93%) as an oil. ESI-MS m/z calc. 332.4. found 333.5 (M+1)+; Retention time: 1.21 minutes (3 min run).

Workup

filtrationThe reaction mixture was filtered through a plug of celite
concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record: ord-d4d1d711c88e4f8b9c310da655efb27c
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181273B2

Reaction notes

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