Water → 1-Methyl-1,2,5,6-tetrahydropyridine-3-methanol

HRID 12500

反応式

HRID 12500 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9]([C:11]1[CH2:12][N:13]([CH3:17])[CH2:14][CH2:15][CH:16]=1)=O.O.[OH-].[Na+]>C1COCC1>[CH3:17][N:13]1[CH2:14][CH2:15][CH:16]=[C:11]([CH2:9][OH:8])[CH2:12]1

参加物

6

反応物 4

HCID 962Water2 回HCID 2230ArecolineHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride

生成物 1

HCID 4247001-Methyl-1,2,5,6-tetrahydropyridine-3-methanol収率 98.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

6.5 g of LiAlH4 (3.2 equiv.) was suspended in 100 mL dry THF and cooled with an ice bath. To this was added dropwise a solution of 8.27 g 1-Methyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester (free base) in 50 mL dry THF. The mixture was stirred for 3 hours at room temperature. The mixture was cooled with an ice bath and 6.5 mL H2O, 13 mL 2 M NaOH and 6.5 mL H2O were added dropwise. The residue was filtered, washed with ether and the filtrate was concentrated in vacuo to yield 6.7 g of a colorless oil. 1H NMR (400 MHz, CDCl3) δ 2.18-2.26 (m, 2H), 2.36 (s, 3H), 2.49 (t, J=6 Hz, 2H), 2.92-2.97 (m, 2H), 4.00 (br s, 2H), 5.68 (br s, 1H).

後処理

  1. temperaturecooled with an ice bath
  2. temperatureThe mixture was cooled with an ice bath
  3. filtrationThe residue was filtered
  4. washwashed with ether
  5. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-2e554649f6b9407aa6af9dc843fd250c
出典データセット
uspto-grants-2010_06
特許番号
US07728018B2

関連ノート

読み込み中…