Ammonium Chloride → Tert-butyl N-[1-(prop-2-ynoyl)cyclopropyl]carbamate

HRID 1688377Notes

Reaction equation

HRID 1688377 reaction equation
CON(C)[C:4]([C:6]1([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:8][CH2:7]1)=[O:5].C[Si]([C:22]#[CH:23])(C)C.[NH4+].[Cl-]>C1COCC1>[C:4]([C:6]1([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:7][CH2:8]1)(=[O:5])[C:22]#[CH:23]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 66111TrimethylsilylacetyleneHCID 15234151Tert-butyl 1-(methoxy(methyl)carbamoyl)cyclopropylcarbamate

Product 1

HCID 86646201Tert-butyl N-[1-(prop-2-ynoyl)cyclopropyl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 1-(methoxy(methyl)carbamoyl)cyclopropylcarbamate (5.0 g, 20.49 mmol, 1.0 eq) in THF at −78° C. was added (trimethylsilyl)acetylene (6.36 g, 61.15 mmol, 3.0 eq), and the stirring continued at the same temperature for 5 hr. Product formation was confirmed by LCMS. Saturated NH4Cl solution was added to the reaction mixture, which was then extracted with EtOAC. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by column chromatography using silica gel (60-120). The desired compound was eluted with 15% EtOAC in Pet ether. Yield: 1.5 g (35.70%).

Workup

  1. extractionwas then extracted with EtOAC
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography
  6. washThe desired compound was eluted with 15% EtOAC in Pet ether

Sources & evidence

ORD record
ord-c3acadd2ded5485681f18384c5e102d3
Source dataset
uspto-grants-2012_04
Patent number
US08148382B2

Reaction notes

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