Tetrahydrofuran → 2-(N-Boc-aminooxy)-2-methylpropan-1-ol

HRID 79001ノート

反応式

HRID 79001 の反応式
C([O:3][C:4](=O)[C:5]([O:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:7])[CH3:6])C.[AlH4-].[Li+].O1CCCC1>C(OCC)C>[C:10]([NH:9][O:8][C:5]([CH3:7])([CH3:6])[CH2:4][OH:3])([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 28112Lithium aluminum hydrideHCID 108243852-(N-Boc-aminooxy)isobutyric acid ethyl ester

生成物 1

HCID 108458992-(N-Boc-aminooxy)-2-methylpropan-1-ol収率 99.5%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2-(N-Boc-aminooxy)isobutyric acid ethyl ester (2.35 g, 9.5 mmol) in anhydrous ethyl ether (100 mL) at 0° C. under nitrogen was added 1.0 M lithiumtetrahydroaluminate in tetrahydrofuran (17.1 mL, 17 mmol), and the reaction mixture stirred at 0° C. for 5 hours. The reaction mixture was quenched with water (25 mL) and allowed to warm to room temperature. The suspension was filtered and the residue washed with diethyl ether and layers separated. The organic extract was dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a white solid (1.94 g, 99%). 1H NMR (CDCl3, 400 MHz) 3.40 (s, 2H), 1.50 (s, 9H), 1.20 (s, 6H).

後処理

  1. customThe reaction mixture was quenched with water (25 mL)
  2. temperatureto warm to room temperature
  3. filtrationThe suspension was filtered
  4. washthe residue washed with diethyl ether and layers
  5. customseparated
  6. extractionThe organic extract
  7. dry with materialwas dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-35e1f6823c8d4c0cacedf4d796d1529d
出典データセット
uspto-grants-2014_09
特許番号
US08841462B2

反応ノート

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