1-Benzyl-3-pyrrolidinone → 1-Benzyl-3-methylpyrrolidin-3-OL

HRID 338831ノート

反応式

HRID 338831 の反応式
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:14][Mg+].[Br-]>C1COCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH3:14])([OH:13])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 698901-Benzyl-3-pyrrolidinoneHCID 178418689HCID 178418689、化合物

生成物 1

HCID 186296481-Benzyl-3-methylpyrrolidin-3-OL収率 56%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 1-benzylpyrrolidin-3-one (9.98 g, 57.0 mmol) in THF (57.0 mL) at −20° C. was added to 1.4M MeMgBr (85.4 mL, 120 mmol). When addition was complete, the ice bath was removed and the reaction was allowed to warm to ambient temperature and then quenched with water (200 mL). The mixture was diluted with saturated NH4Cl (200 mL) and ethyl acetate (300 mL) and stirred vigorously for 5 minutes. An inseparable emulsion formed with fine particulates. The reaction mixture was filtered under vacuum and the layers were separated. The aqueous layer was extracted with ethyl acetate (200 mL) and the organic layer was washed with brine (100 mL), dried (MgSO4), filtered and concentrated under reduced pressure to an oil which was purified by flash chromatography (0-5% Methanol/DCM) to give (+/−)1-benzyl-3-methylpyrrolidin-3-ol (6.10 g, 31.9 mmol, 56.0% yield).

後処理

  1. additionWhen addition
  2. customthe ice bath was removed
  3. customquenched with water (200 mL)
  4. additionThe mixture was diluted with saturated NH4Cl (200 mL) and ethyl acetate (300 mL)
  5. customAn inseparable emulsion formed with fine particulates
  6. filtrationThe reaction mixture was filtered under vacuum
  7. customthe layers were separated
  8. extractionThe aqueous layer was extracted with ethyl acetate (200 mL)
  9. washthe organic layer was washed with brine (100 mL)
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure to an oil which
  13. customwas purified by flash chromatography (0-5% Methanol/DCM)

出典と根拠

ORDレコード
ord-fbff5070666d43c089dc2c9a57df141b
出典データセット
uspto-grants-2014_11
特許番号
US08889704B2

反応ノート

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