Nitroethane → HCID 67051851, 화합물

HRID 1809016노트

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HRID 1809016 반응식
[H-].[Na+].[N+:3]([CH2:6][CH3:7])([O-:5])=[O:4].[O:8]=[C:9]1[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]1>O1CCCC1>[OH:8][C:9]1([CH:6]([N+:3]([O-:5])=[O:4])[CH3:7])[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]1

참가 물질

5

반응물 3

HCID 6587NitroethaneHCID 24758Sodium hydrideHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 67051851HCID 67051851, 화합물수율 58.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a suspension of sodium hydride (72 mg, 1.75 mmol, 60% wt) in tetrahydrofuran (1 mL) cooled to 0° C. was added nitroethane (125 μL, 1.75 mmol). The suspension was allowed to warm to room temperature and was stirred for 15 minutes, then cooled back to 0° C. To the suspension was added dropwise a solution of 1,1-dimethylethyl 3-oxoazetidine-1-carboxylate (300 mg, 1.75 mmol, in 2 mL of tetrahydrofuran), prepared using procedures similar to those described in Reference 3. The suspension was stirred at room temperature for 1 hour. The reaction mixture was quenched by adding 20% aqueous citric acid, and then was partitioned with ethyl acetate. The aqueous portion was extracted twice using ethyl acetate and the combined organic portion was washed with saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford a colorless oil that was purified by column chromatography. Eluting with 30% ethyl acetate in hexanes, the isolated product was concentrated in vacuo to afford 250 mg, 1.02 mmol (58%) of 1,1-dimethylethyl 3-hydroxy-3-(1-nitroethyl)azetidine-1-carboxylate as a colorless oil. 1H NMR (400 MHz, DMSO): 6.46 (s, 1H), 5.01 (q, 1H), 4.24-3.97 (m, 2H), 3.77-3.60 (m, 2H), 1.41 (d, 3H), 1.39 (s, 9H).

후처리

  1. temperatureto warm to room temperature
  2. temperaturecooled back to 0° C
  3. customprepared
  4. stirringThe suspension was stirred at room temperature for 1 hour
  5. customThe reaction mixture was quenched
  6. additionby adding 20% aqueous citric acid
  7. customwas partitioned with ethyl acetate
  8. extractionThe aqueous portion was extracted twice using ethyl acetate
  9. washthe combined organic portion was washed with saturated sodium bicarbonate, brine
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customto afford a colorless oil that
  14. customwas purified by column chromatography
  15. washEluting with 30% ethyl acetate in hexanes
  16. concentrationthe isolated product was concentrated in vacuo

출처 및 근거

ORD 기록
ord-e8e9ec29a0314484b79d81b80766c159
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362002B2

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