Nitroethane → HCID 67051851, compound

HRID 1809016Notes

Reaction equation

HRID 1809016 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 67051851HCID 67051851, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-e8e9ec29a0314484b79d81b80766c159
Source dataset
uspto-grants-2013_01
Patent number
US08362002B2

Reaction notes

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