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

HRID 12500노트

반응식

HRID 12500 반응식
[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

참가 물질

6

반응물 4

HCID 962Water2회HCID 2230ArecolineHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2e554649f6b9407aa6af9dc843fd250c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728018B2

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