Ethyl 3-(4-benzylpiperidin-1-yl)butyrate → 4-Benzyl-1-(3-hydroxy-1-methylpropyl)piperidine

HRID 1861776

반응식

HRID 1861776 반응식
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH:14]([CH3:21])[CH2:15][C:16](OCC)=[O:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([CH:8]1[CH2:9][CH2:10][N:11]([CH:14]([CH3:21])[CH2:15][CH2:16][OH:17])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 18621512Ethyl 3-(4-benzylpiperidin-1-yl)butyrateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 129729654-Benzyl-1-(3-hydroxy-1-methylpropyl)piperidine수율 80%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

To a solution of ethyl 3-(4-benzylpiperidin-1-yl)butyrate (0.60 g, 2.0 mmol) in dry THF (10 mL) was added portionwise LiAlH4 (0.15 g, 3.9 mmol). The resulting heterogeneous mixture was stirred at 25° C. for 2 h then quenched with MeOH. The resulting mixture was diluted with EtOAc (100 mL), washed with NH4Cl (100 mL) and brine (100 mL), dried and was concentrated under reduced pressure. The crude compound was purified by filtration on silica gel using CH2Cl2/MeOH as solvent to afford the title compound as a colorless solid (0.38 g, 80%): mp 74-76° C.; 1H NMR (CDCl3) δ1.00 (d, J=6.6 Hz, 3H), 1.15-1.45 (m, 3H), 1.50-1.65 (m, 1H), 1.65-1.80 (m, 2H), 1.85-2.15 (m, 3H), 2.40-2.60 (m, 3H), 2.82 (bd, J=11.1 Hz, 1H), 2.90-3.10 (m, 2H), 3.80-4.00 (m, 2H), 6.55 (bs, 1H), 7.19 (t, J=7.2 Hz, 2H), 7.24 (d, J=6.9 Hz, 1H), 7.32 (t, J=7.2 Hz, 2H); MS (m/z) 247, 248, 232, 202, 91. Anal. Calcd for C16H25NO: C, 77.68, H 10.18; N, 5.66. Found C, 77.56; H 10.22; N, 5.63.

후처리

  1. customthen quenched with MeOH
  2. additionThe resulting mixture was diluted with EtOAc (100 mL)
  3. washwashed with NH4Cl (100 mL) and brine (100 mL)
  4. customdried
  5. concentrationwas concentrated under reduced pressure
  6. filtrationThe crude compound was purified by filtration on silica gel

출처 및 근거

ORD 기록
ord-d041f354dfe94a9dacf2055371649c04
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06534522B2

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