Ammonium formate → (4-Isopropoxy-3-methoxy-phenyl)-(9-phenyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)methanone

HRID 73028Notes

Reaction equation

[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([N:13]2[CH2:18][CH2:17][C:16]3([O:23][CH2:22][CH:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:20](CC4C=CC(OC)=CC=4)[CH2:19]3)[CH2:15][CH2:14]2)=[O:12])=[CH:7][C:6]=1[O:39][CH3:40])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>[OH-].[OH-].[Pd+2].C(O)C>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([N:13]2[CH2:14][CH2:15][C:16]3([O:23][CH2:22][CH:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[NH:20][CH2:19]3)[CH2:17][CH2:18]2)=[O:12])=[CH:7][C:6]=1[O:39][CH3:40])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 65 °C

Procedure

To (4-isopropoxy-3-methoxy-phenyl)-[8-[(4-methoxyphenyl)methyl]-9-phenyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]methanone (175 mg, 0.32 mmol), Pd(OH)2 (129 mg, 0.9186 mmol) and ammonium formate (405 mg, 6.43 mmol) was added ethanol. The reaction mixture was then heated at 65° C. for 16 hours. The reaction mixture was filtered, the solvent evaporated and the residue was purified by silica gel column chromatography using 0 to 60% EtOAc in hexanes as eluent to give (4-isopropoxy-3-methoxy-phenyl)-(9-phenyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)methanone. ESI-MS m/z calc. 424.5. Found 425.5 (M+1)+; Retention time: 1.28 minutes (3 min run).

Workup

filtrationThe reaction mixture was filtered
customthe solvent evaporated
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-af67d2af46b94b2baa91ab94f6721af7
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828996B2

Reaction notes

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