Pyridine → N-(1,4-Dioxaspiro[4,5]dec-8-yl)-2,2,N-trimethylpropionamide

HRID 1748613Notes

Reaction equation

[O:1]1[C:5]2([CH2:10][CH2:9][CH:8](CN)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[C:13]([O:19]C(=O)C(C)(C)C)(=O)[C:14]([CH3:17])([CH3:16])[CH3:15].[N:26]1C=CC=C[CH:27]=1>CN(C)C1C=CN=CC=1>[O:4]1[C:5]2([CH2:6][CH2:7][CH:8]([N:26]([CH3:27])[C:13](=[O:19])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of (1,4-dioxaspiro[4,5]dec-8-yl)methylamine (11.0 g) in pyridine (64 ml) were added 4-dimethylaminopyridine (catalyst quantity) and pivalic acid anhydride (26.0 ml), and stirred at 90° C. for 2 hours. After completion of the reaction, the solvent was evaporated, ethyl acetate was added thereto, and sequentially washed with 1 N hydrochloric acid aqueous solution, 1 N aqueous solution of sodium hydroxide, and saturated brine. The organic layer was dried over sodium sulfate, then the solvent was evaporated, and the obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give the titled compound (12.9 g) as a pale brown oil. MS (ESI) m/z: 256 (M+H)+.

Workup

customAfter completion of the reaction
customthe solvent was evaporated
additionethyl acetate was added
washsequentially washed with 1 N hydrochloric acid aqueous solution, 1 N aqueous solution of sodium hydroxide, and saturated brine
dry with materialThe organic layer was dried over sodium sulfate
customthe solvent was evaporated
customthe obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record: ord-f97e50e5072c4820af1c28a4db81b237
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150555B2

Reaction notes

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