Methyl iodide → HCID 86709522, compound

HRID 1848529Notes

Reaction equation

[OH:1][CH:2]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17][CH2:16][C:3]21[C:7](=[O:8])[N:6]([C:9]1[CH2:10][O:11][C:12](=[O:15])[C:13]=1[CH3:14])[CH2:5][CH2:4]2.[CH3:27]I>C(#N)C.[Ag]=O>[CH3:27][O:1][CH:2]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17][CH2:16][C:3]21[C:7](=[O:8])[N:6]([C:9]1[CH2:10][O:11][C:12](=[O:15])[C:13]=1[CH3:14])[CH2:5][CH2:4]2

Participants

Conditions

Temperature: 60 °C

Procedure

To the mixture of tert-butyl 6-hydroxy-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (CIS) (2 g, 5.46 mmol) and silver oxide (1.391 g, 6.00 mmol) in acetonitrile (50 mL) was added methyl iodide (3.41 ml, 54.6 mmol). The mixture was heated at 60° C. in a sealed tube overnight. After it cooled to rt, the mixture was filtered and the filtrate was concentrated and the residue was purified by silica gel chromatography using ethyl acetate/hexane to give tert-butyl 6-methoxy-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (CIS, racemate). LC/MS: (M+1)+: 380.99. The racetmate was further separated on an AD chiral column give tert-butyl 6-methoxy-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (faster eluting, CIS), LC/MS: (M+1)+: 381.05, and tert-butyl 6-methoxy-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (slower eluting, CIS). LC/MS: (M+1)+: 381.01.

Workup

temperatureAfter it cooled to rt
filtrationthe mixture was filtered
concentrationthe filtrate was concentrated
customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-7e99e6dc175a4e1ab9c54579d0268ca9
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952166B2

Reaction notes

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