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

HRID 1748613
ノート
印刷プレビュー

反応式

HRID 1748613 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1049PyridineHCID 15234Pivalic anhydrideHCID 109539781-{1,4-Dioxaspiro[4.5]decan-8-yl}methanamine

生成物 1

HCID 79111757N-(1,4-Dioxaspiro[4,5]dec-8-yl)-2,2,N-trimethylpropionamide

試薬・触媒・溶媒 1

HCID 142844-(Dimethylamino)pyridine触媒

反応条件

温度
90 °C

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-f97e50e5072c4820af1c28a4db81b237
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09150555B2

反応ノート

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