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

HRID 1748613
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HRID 1748613 반응식
[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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine촉매

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온도
90 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-f97e50e5072c4820af1c28a4db81b237
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09150555B2

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