1,1-Dimethylethyl N-[(1R)-1-ethyl-3-oxopropyl]carbamate → HCID 15881262, compound

HRID 409469Notes

Reaction equation

HRID 409469 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]([CH2:12][CH3:13])[CH2:9][CH:10]=[O:11])([CH3:4])([CH3:3])[CH3:2].[CH:15]([Mg]Cl)=[CH2:16]>C1COCC1>[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]([CH2:12][CH3:13])[CH2:9][C@H:10]([OH:11])[CH:15]=[CH2:16])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 111716571,1-Dimethylethyl N-[(1R)-1-ethyl-3-oxopropyl]carbamateHCID 178461836HCID 178461836, compound2×

Product 1

HCID 15881262HCID 15881262, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of ((R)-1-ethyl-3-oxo-propyl)carbamic acid tert-butyl ester (2.9 mmol; 584 mg) in THF (20 mL) is added a 1.44 M THF solution (11.6 mmol; 8.1 mL) of vinylmagnesium chloride under nitrogen at −78° C. After stirring for 30 minutes, the reaction mixture is warmed to room temperature and stirred for an additional 1.5 hours. Another 1.44 M THF solution (2.9 mmol; 2 mL) of vinylmagnesium chloride is added to the reaction mixture at room temperature. After stirring for additional 15 minutes, the solution is quenched by saturated aqueous ammonium chloride solution and extracted three times with EtOAc. The combined organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (eluent; n-hexane/EtOAc) to give ((1R,3S)-1-ethyl-3-hydroxy-pent-4-enyl)-carbamic acid tert-butyl ester (130 mg, 20%); ESI-MS m/z: 174 [M+−tBu+2], Retention time 4.13 min (condition B).

Workup

  1. stirringstirred for an additional 1.5 hours
  2. stirringAfter stirring for additional 15 minutes
  3. customthe solution is quenched by saturated aqueous ammonium chloride solution
  4. extractionextracted three times with EtOAc
  5. washThe combined organic layer is washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is purified by column chromatography on silica gel (eluent; n-hexane/EtOAc)

Sources & evidence

ORD record
ord-df32942678b84e07969b93a75aba4525
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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