3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → Tert-butyl 3-allyl-3-hydroxyazetidine-1-carboxylate

HRID 403504ノート

反応式

HRID 403504 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10](=[O:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:13]([Mg]Br)[CH:14]=[CH2:15]>CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:9][C:10]([CH2:15][CH:14]=[CH2:13])([OH:12])[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 178455850HCID 178455850、化合物

生成物 1

HCID 68378947Tert-butyl 3-allyl-3-hydroxyazetidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

3-Oxo-azetidine-1-carboxylic acid tert-butyl ester (1.37 g, 8 mmol) was dissolved in Et2O (10 ml) and a 1M solution of allylmagnesiumbromid in Et2O (10.4 ml, 10.4 mmol) was added dropwise at 0° C. Stirring was continued at rt overnight. The reaction mixture was quenched with H2O, extracted twice with EtOAc, the organic layer were washed with brine, combined, dried over Na2 SO4, filtered off and concentrated under reduced pressure to give a orange oil. The crude product was purified by flash chromatography (silica gel, EtOAc/cyclohexane 15-25%) which furnished the product as an yellow oil.

後処理

  1. customThe reaction mixture was quenched with H2O
  2. extractionextracted twice with EtOAc
  3. washthe organic layer were washed with brine
  4. customdried over Na2 SO4
  5. filtrationfiltered off
  6. concentrationconcentrated under reduced pressure
  7. customto give a orange oil
  8. customThe crude product was purified by flash chromatography (silica gel, EtOAc/cyclohexane 15-25%) which

出典と根拠

ORDレコード
ord-13bb9bf31e254e34af46bf6d82ac4859
出典データセット
uspto-grants-2014_06
特許番号
US08748435B2

反応ノート

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