Sodium Hydroxide → 1-[3-(Hydroxymethyl)-1-piperidinyl]-3-methyl-1-butanone

HRID 2280181노트

반응식

HRID 2280181 반응식
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][OH:8])[CH2:2]1.[OH-].[Na+].[CH3:11][CH:12]([CH3:17])[CH2:13][C:14](Cl)=[O:15]>O.C1COCC1.CCOCC>[OH:8][CH2:7][CH:3]1[CH2:4][CH2:5][CH2:6][N:1]([C:14](=[O:15])[CH2:13][CH:12]([CH3:17])[CH3:11])[CH2:2]1

참가 물질

7

반응물 3

HCID 14798Sodium HydroxideHCID 66054Isovaleryl chlorideHCID 107308Piperidin-3-ylmethanol

생성물 1

HCID 434223971-[3-(Hydroxymethyl)-1-piperidinyl]-3-methyl-1-butanone수율 94%

시약·촉매·용매 3

HCID 962Water용매2회HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of piperidin-3-ylmethanol (10 g, 86.83 mmol) in water (25 mL), was added a solution of NaOH (13.89 g, 347.31 mmol) in water (25 mL) dropwise at 0° C. The mixture was stirred for 15 minutes, after which time, a solution of 3-methylbutanoyl chloride (20.94 g, 173.66 mmol) in THF (25 mL) was added dropwise with vigorous stirring. The reaction was slowly warmed to room temperature and, upon completion was diluted with Et2O (500 mL) was added with vigouous stirring. After 15 minutes, the phases were separated, and the aqueous phase was extracted with Et2O (2×). The combined organic extracts were washed with brine, dried over Na2SO4, concentrated under reduced pressure and flash chromatographed on silica gel (0-100% EtOAc in hexanes) to give the title compound as a colorless oil (16.27 g, 94%). MS 200 (MH+).

후처리

  1. additionwas added with vigouous stirring
  2. waitAfter 15 minutes
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted with Et2O (2×)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure and flash
  8. customchromatographed on silica gel (0-100% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-44cf17c453484116a8c9a95e9302e2ec
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09138013B2

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