Ammonium formate → (10-Ethyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)-(4-isopropoxy-3-methyl-phenyl)methanone

HRID 73031Notes

Reaction equation

C([N:8]1[CH2:31][CH:30]([CH:32]=[CH2:33])[O:29][C:10]2([CH2:15][CH2:14][N:13]([C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[C:20]([CH3:28])[CH:19]=3)=[O:17])[CH2:12][CH2:11]2)[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[CH2:32]([CH:30]1[O:29][C:10]2([CH2:15][CH2:14][N:13]([C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:26])[CH3:27])=[C:20]([CH3:28])[CH:19]=3)=[O:17])[CH2:12][CH2:11]2)[CH2:9][NH:8][CH2:31]1)[CH3:33]

Participants

Conditions

Temperature: 75 °C

Procedure

To (8-benzyl-10-vinyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)-(4-isopropoxy-3-methyl-phenyl)methanone (150 mg, 0.33 mmol), ammonium formate (74 mg, 1.17 mmol) and Pd (17 mg, 0.02 mmol) (10% on activated carbon) was added methanol (2 mL) and the reaction mixture was heated at 75° C. for 30 minutes. The reaction mixture was cooled, microfiltered and concentrated in vacuo, then diluted with DCM (20 mL), washed with aq. 1M NaOH (10 mL), extracted with DCM (120 mL), washed with brine (10 mL), dried over MgSO4 and concentrated in vacuo to give (10-ethyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)-(4-isopropoxy-3-methyl-phenyl)methanone (100 mg, 83%) as a colorless oil. ESI-MS m/z calc. 360.5. Found 361.3 (M+1)+; Retention time: 1.25 minutes (3 min run).

Workup

temperatureThe reaction mixture was cooled
concentrationmicrofiltered and concentrated in vacuo
additiondiluted with DCM (20 mL)
washwashed with aq. 1M NaOH (10 mL)
extractionextracted with DCM (120 mL)
washwashed with brine (10 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d144cd09ffb04ac4b17a0acc6cc7b60b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828996B2

Reaction notes

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