(R)-1-(3-methylbutanoyl)piperidine-3-carboxylic acid → (R)-1-(3-(hydroxymethyl)piperidin-1-yl)-3-methylbutan-1-one

HRID 1483984ノート

反応式

HRID 1483984 の反応式
[CH3:1][CH:2]([CH3:15])[CH2:3][C:4]([N:6]1[CH2:11][CH2:10][CH2:9][C@@H:8]([C:12](O)=[O:13])[CH2:7]1)=[O:5]>C1COCC1>[OH:13][CH2:12][C@@H:8]1[CH2:9][CH2:10][CH2:11][N:6]([C:4](=[O:5])[CH2:3][CH:2]([CH3:1])[CH3:15])[CH2:7]1

参加物

3

反応物 1

HCID 42257258(R)-1-(3-methylbutanoyl)piperidine-3-carboxylic acid

生成物 1

HCID 28345459(R)-1-(3-(hydroxymethyl)piperidin-1-yl)-3-methylbutan-1-one収率 7.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (R)-1-(3-methylbutanoyl)piperidine-3-carboxylic acid (Example 34d) (2.52 g, 11.84 mmol) in THF (20 mL) at 0° C., was added BH3Me2S (1.2 mL, 13.0 mmol) dropwise over 15 minutes. The reaction was warmed to room temperature and stirred overnight, cooled to 0° C., quenched with water, concentrated under reduced pressure to remove THF and extracted with EtOAc. The combined extracts were washed with saturated aqueous NaHCO3, dried over Na2SO4, filtered, concentrated under reduced pressure and purified by flash chromatography on silica gel (EtOAc/hexanes) to give the title compound (184 mg, 6%). MS 200 (MH+).

後処理

  1. temperaturecooled to 0° C.
  2. customquenched with water
  3. concentrationconcentrated under reduced pressure
  4. customto remove THF
  5. extractionextracted with EtOAc
  6. washThe combined extracts were washed with saturated aqueous NaHCO3
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. custompurified by flash chromatography on silica gel (EtOAc/hexanes)

出典と根拠

ORDレコード
ord-666b3569237f44488884bf6251230ac4
出典データセット
uspto-grants-2016_08
特許番号
US09420814B2

反応ノート

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