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

HRID 403504노트

반응식

HRID 403504 반응식
[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]

참가 물질

4

반응물 2

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 178455850HCID 178455850, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-13bb9bf31e254e34af46bf6d82ac4859
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748435B2

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