Water → (R)-(1-Methylpiperidin-2-yl)methanol

HRID 1923412

반응식

HRID 1923412 반응식
C(N[C:4]([N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@@H:7]1[C:12](O)=[O:13])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:4][N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@@H:7]1[CH2:12][OH:13]

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 54508361(R)-1-Ethylcarbamoylpiperidine-2-carboxylic acid

생성물 1

HCID 853004(R)-(1-Methylpiperidin-2-yl)methanol수율 80%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

The product of Step 1 (0.60 g, 0.003 mole) in dry tetrahydrofuran (10 ml) was added dropwise to a suspension of lithium aluminium hydride (0.57 g, 0.015 mole) in dry tetrahydrofuran (20 ml). The mixture was heated under reflux for 2 hours and stirred at room temperature overnight. The reaction mixture was cooled to 0° C. and water (0.5 ml) was added dropwise, followed by 10% sodium hydroxide solution (0.9 ml) and water (1.4 ml). The mixture was stirred for 1 hour, filtered through Celite and the filtrate evaporated in vacuo to afford the title compound 0.31 g (80%) as a pale yellow oil; 1H NMR (CDCl3) 1.17-2.00 (8H, m), 2.14 (1H, dt, J 13 and 2 Hz), 2.30 (3H, s), 2.76-2.96 (1H, m), 3.40 (1H, dd, J 13 and 1 Hz), 3.88 (1H, dd, J 12 and 5 Hz); MS (+ve ion electrospray) m/z 130 (MH+).

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. stirringThe mixture was stirred for 1 hour
  5. filtrationfiltered through Celite
  6. customthe filtrate evaporated in vacuo

출처 및 근거

ORD 기록
ord-dc3d728f53184fbea939fb14dd6af026
출처 데이터셋
uspto-grants-2012_05
특허 번호
USRE043390E1

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