Tetrahydrofuran → Ethyl (2E)-5-(tert-butoxycarbonylamino)5-methylhex-2-enoate

HRID 2104311Notes

Reaction equation

HRID 2104311 reaction equation
C[C:2]([CH3:5])([O-:4])C.[K+].[C:7]([O:11][C:12]([NH:14][C:15]([CH3:20])([CH3:19])[CH2:16][CH:17]=O)=[O:13])([CH3:10])([CH3:9])[CH3:8].[O:21]1CC[CH2:23][CH2:22]1>C(OCC)(=O)C.Cl>[C:7]([O:11][C:12]([NH:14][C:15]([CH3:20])([CH3:19])[CH2:16]/[CH:17]=[CH:23]/[C:22]([O:4][CH2:2][CH3:5])=[O:21])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 11788901tert-butyl N-(2-methyl-4-oxobutan-2-yl)carbamateHCID 23665647Potassium tert-butoxide

Product 1

HCID 10540052Ethyl (2E)-5-(tert-butoxycarbonylamino)5-methylhex-2-enoate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylphoshonoacetate (1.96 ml, 9.8 mmol) was dissolved in tetrahydrofuran (30 ml). Potassium tert-butoxide (1.10 g, 9.8 mmol) was added. The solution was stirred for 40 min at room temperature. A solution of 3-(tert-butoxycarbonylamino)-3-methylbutanal (1.10 g, 5.5 mmol) in Tetrahydrofuran (6 ml) was added. The solution was stirred at room temperature. for 75 min. It was diluted with ethyl acetate (100 ml) and 1N hydrochloric acid (100 ml). The phases were separated. The aqueous phase was extracted with ethyl acetate (2×50 ml). The combined organic phases were washed with saturated sodium hydrogen carbonate solution (60 ml) and dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by column chromatography on silica (90 g) with ethyl acetate/hepatane (1:4) to give 1.27 g of ethyl (2E)-5-(tert-butoxycarbonylamino)-5-methylhex-2-enoate.

Workup

  1. stirringThe solution was stirred at room temperature
  2. waitfor 75 min
  3. customThe phases were separated
  4. extractionThe aqueous phase was extracted with ethyl acetate (2×50 ml)
  5. washThe combined organic phases were washed with saturated sodium hydrogen carbonate solution (60 ml)
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed in vacuo
  8. customThe crude product was purified by column chromatography on silica (90 g) with ethyl acetate/hepatane (1:4)

Sources & evidence

ORD record
ord-5558479d72034000ad5a86d6735a9c7c
Source dataset
uspto-grants-2009_08
Patent number
US07576062B2

Reaction notes

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