Sodium Hydroxide → (1-Isopropylpiperidin-4-yl)methanol

HRID 131276ノート

反応式

HRID 131276 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([N:10]1[CH2:15][CH2:14][CH:13]([C:16](OCC)=[O:17])[CH2:12][CH2:11]1)([CH3:9])[CH3:8].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.O>[CH:7]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][OH:17])[CH2:12][CH2:11]1)([CH3:9])[CH3:8]

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 19900430Ethyl 1-isopropylpiperidine-4-carboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 11147855(1-Isopropylpiperidin-4-yl)methanol収率 99%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

Under argon gas atmosphere, lithium aluminum hydride (3.29 g) is suspended in tetrahydrofuran (160 mL) and thereto is added ethyl 1-isopropylpiperidin-4-carboxylate (compound obtained in Reference Example 94(1), 5.00 g) under ice-cooling. The mixture is stirred at room temperature for 14 hours. To the reaction mixture is added successively water (3.3 mL), 2N sodium hydroxide solution (6.6 mL) and water (6.6 mL) under ice-cooling. The mixture is stirred at room temperature for 1 hour. After addition of magnesium sulfate, the reaction mixture is stirred for 10 minutes and filtered. The filtrate is concentrated in vacuo and the residue is purified by flash column chromatography on NH-silica gel (Solvent; n-hexane:ethyl acetate=1:1) to give (1-isopropylpiperidin-4-yl)methanol (3.75 g, yield; 99%) as a colorless oil. MS (APCI) m/z: 158 [M+H]+

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. stirringThe mixture is stirred at room temperature for 1 hour
  4. stirringthe reaction mixture is stirred for 10 minutes
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated in vacuo
  7. customthe residue is purified by flash column chromatography on NH-silica gel (Solvent; n-hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-77b9a00a81bf47ae8de9da058da97263
出典データセット
uspto-grants-2008_06
特許番号
US07384952B2

反応ノート

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