1-Oxaspiro[2.5]octane → HCID 11351106, compound

HRID 1809362Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[O:14])[C:5](=[O:12])[N:6]([CH:9]([CH3:11])[CH3:10])[C:7]=1[CH3:8].[O:23]1[C:25]2([CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:24]1>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:24][C:25]3([OH:23])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH2:19][CH2:18]2)=[O:14])[C:5](=[O:12])[N:6]([CH:9]([CH3:10])[CH3:11])[C:7]=1[CH3:8]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 5-chloro-1-isopropyl-6-methyl-2-oxo-N-(piperidin-4-ylmethyl)-1,2-dihydropyridine-3-carboxamide as prepared in Example 6(2) (484 mg, 1.49 mmol) and 1-oxaspiro[2.5]octane (200 mg, 1.78 mmol, prepared according to Blake, Alexander J et al., J. Chem. Soc. Dalton Trans., 1998, 14, 2335) in methanol (5 mL) was stirred at 50° C. for 16 h. Then, the solvent was removed in vacuo. The residue was chromatographed on a column of silica gel eluting with dichloromethane/methanol (v/v=20/1) to give 751 mg (99%) of the title compound as a white solid.

Workup

customThen, the solvent was removed in vacuo
customThe residue was chromatographed on a column of silica gel eluting with dichloromethane/methanol (v/v=20/1)

Sources & evidence

ORD record: ord-903c7ed405054dde940a1028ad435b35
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362038B2

Reaction notes

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