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

HRID 2280181ノート

反応式

HRID 2280181 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-44cf17c453484116a8c9a95e9302e2ec
出典データセット
uspto-grants-2015_09
特許番号
US09138013B2

反応ノート

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