Water → 1-(2-Phenylethyl)-4-methyl-4-hydroxymethyl-piperidine

HRID 374464ノート

反応式

HRID 374464 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][C:18]([CH3:26])([C:21](OCC)=[O:22])[CH2:17][CH2:16]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[OH-].[Na+]>C1COCC1>[C:7]1([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][C:18]([CH3:26])([CH2:21][OH:22])[CH2:17][CH2:16]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 18997143HCID 18997143、化合物HCID 21226445Aluminium lithium hydride

生成物 1

HCID 189971411-(2-Phenylethyl)-4-methyl-4-hydroxymethyl-piperidine収率 95%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of 0.51 g (13.4 mmol) of lithium aluminum hydride in 20 mL of THF under nitrogen was added dropwise a solution of 3.70 g (13.4 mmol) of 1-(2-phenylethyl)-4-methyl-4-carboethoxypiperidine in 15 mL of THF. The solution was heated at reflux for 3 hours. To the cooled reaction mixture (ice bath) was slowly added 0.5 mL of water, followed by 0.5 mL of 15% sodium hydroxide followed by 1.5 mL of water. The precipitated lithium salts were removed by filtration. The filtrate was evaporated to dryness. The residue was reconstituted in methylene chloride, washed with a small amount of water, dried and evaporated to afford 2.97 g of 1-(2-phenylethyl)-4-methyl-4-hydroxymethyl-piperidine as a yellow oil. NMR (CDCl3) δ7.16-7.23 (m, 5H); 3.40 (s, 2H); 2.79-2.87 (m, 2H); 2.57-2.71 (m, 4H); 2.31-2.42 (m, 2H); 1.57-1.63 (m, 5H); 0.97 (s, 3H).

後処理

  1. temperatureThe solution was heated
  2. temperatureat reflux for 3 hours
  3. customTo the cooled reaction mixture (ice bath)
  4. customThe precipitated lithium salts were removed by filtration
  5. customThe filtrate was evaporated to dryness
  6. washwashed with a small amount of water
  7. customdried
  8. customevaporated

出典と根拠

ORDレコード
ord-9d0c5baae47440b693588d284c4ececf
出典データセット
uspto-grants-1996_01
特許番号
US05480892

反応ノート

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