Tetrahydrofuran → Carbamic acid, methyl[2-(methylthio)ethyl]-, 1,1-dimethylethyl ester

HRID 350714Notes

Reaction equation

HRID 350714 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+].O1CCC[CH2:37]1>>[CH3:37][N:5]([CH2:4][CH2:3][S:2][CH3:1])[C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 62649Sodium sulfate decahydrateHCID 4145154Tert-Butyl (2-(methylthio)ethyl)carbamateHCID 21226445Aluminium lithium hydride

Product 1

HCID 23061816Carbamic acid, methyl[2-(methylthio)ethyl]-, 1,1-dimethylethyl ester

Procedure

To a mixture of tert-butyl 2-(methylsulfanyl)ethylcarbamate (3.5 g) and tetrahydrofuran (20 mL) was added lithium aluminum hydride (1.39 g) with stirring under ice-cooling and the mixture was heated under reflux for 2 hrs. After cooling the reaction mixture, sodium sulfate 10 hydrate (5 g) was added, and the solid was filtered off. The filtrate was concentrated and diluted with tetrahydrofuran, and di-tert-butyl dicarbonate was added dropwise with stirring under ice-cooling. After stirring at room temperature for 30 min, the reaction mixture was concentrated, diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and tert-butyl N-methyl-N-[2-(methylsulfanyl)ethyl]carbamate was obtained as a colorless oil (0.82 g, yield 22%) from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio).

Workup

  1. temperaturecooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hrs
  4. additionwas added
  5. filtrationthe solid was filtered off
  6. concentrationThe filtrate was concentrated
  7. additiondiluted with tetrahydrofuran, and di-tert-butyl dicarbonate
  8. additionwas added dropwise
  9. stirringwith stirring under ice-
  10. temperaturecooling
  11. stirringAfter stirring at room temperature for 30 min
  12. concentrationthe reaction mixture was concentrated
  13. additiondiluted with ethyl acetate
  14. washwashed with water
  15. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  16. concentrationconcentrated

Sources & evidence

ORD record
ord-7492909691354d93aaeead8bbd7977fe
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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