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Diethyl P-(1-phenylethyl)phosphonate → (S)-2,2-dimethyl-4-((E)-2-phenyl-propenyl)-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 1911504
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HRID 1911504 반응식
CCOP(OCC)([CH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:7])=O.C([Li])CCC.[C:22]([O:26][C:27]([N:29]1[C@@H:33]([CH:34]=O)[CH2:32][O:31][C:30]1([CH3:37])[CH3:36])=[O:28])([CH3:25])([CH3:24])[CH3:23]>COCCOC>[C:22]([O:26][C:27]([N:29]1[C@@H:33](/[CH:34]=[C:6](/[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)\[CH3:7])[CH2:32][O:31][C:30]1([CH3:36])[CH3:37])=[O:28])([CH3:25])([CH3:23])[CH3:24]
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참가 물질

5

반응물 3

HCID 99789Diethyl P-(1-phenylethyl)phosphonateHCID 1787923-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)-HCID 178418339Butyllithium

생성물 1

HCID 68710162(S)-2,2-dimethyl-4-((E)-2-phenyl-propenyl)-oxazolidine-3-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매2회

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온도
0 °C

실험 절차

A solution of diethyl 1-phenylethyl phosphonate (2.35 ml) in 1,2-dimethoxyethane (15 ml) was cooled under an argon atmosphere to 0° C. and treated dropwise with an n-butyllithium solution (5.9 ml; 1.6 M in hexane). The reaction mixture was stirred for 5 min at 0° C., then treated dropwise with a solution of (R)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (1.5 g) in 1,2-dimethoxyethane (15 ml). The solution was warmed to r.t., then refluxed overnight. After cooling to r.t., the mixture was quenched with water and extracted with EtOAc. The organic layer was dried over MgSO4, filtrated and concentrated. The crude product was isolated by column chromatography (SiO2; gradient: cyclohexane ->cyclohexane/EtOAc 1:1) to give (S)-2,2-dimethyl-4-((E)-2-phenyl-propenyl)-oxazolidine-3-carboxylic acid tert-butyl ester (720 mg) as light yellow viscous oil.

후처리

  1. temperatureThe solution was warmed to r.t.
  2. temperaturerefluxed overnight
  3. temperatureAfter cooling to r.t.
  4. customthe mixture was quenched with water
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltrated
  8. concentrationconcentrated
  9. customThe crude product was isolated by column chromatography (SiO2; gradient: cyclohexane ->cyclohexane/EtOAc 1:1)

출처 및 근거

ORD 기록
ord-c2e25b2159f046ce957ed7b3d4573e1e
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08604061B2

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