HCID 57514175, compound → HCID 87170229, compound

HRID 1912451Notes

Reaction equation

HRID 1912451 reaction equation
[C:1]([Mg]Br)#[CH:2].[C:5]([O:9][C:10](=[O:23])[NH:11][C:12]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Br:22])[CH:17]=1)([CH3:15])[CH:13]=[O:14])([CH3:8])([CH3:7])[CH3:6]>C1COCC1.[NH4+].[Cl-]>[C:5]([O:9][C:10](=[O:23])[NH:11][C:12]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Br:22])[CH:17]=1)([CH3:15])[CH:13]([OH:14])[C:1]#[CH:2])([CH3:6])([CH3:7])[CH3:8]

Participants

5

Reactant 2

HCID 57514175HCID 57514175, compoundHCID 178418486HCID 178418486, compound

Product 1

HCID 87170229HCID 87170229, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

Ethynylmagnesium bromide 0.5 M in THF (23.89 mL, 11.94 mmol) was added dropwise to a solution of rac-[1-(3-bromo-phenyl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester (1.96 g, 5.97 mmol) in THF (60 mL) at 0° C. under nitrogen. The mixture was stirred at 0° C. for 15 minutes and at room temperature for 30 minutes. The mixture was diluted with NH4Cl (aq. sat. solution) and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo to yield rac-[1-(3-bromo-phenyl)-2-hydroxy-1-methyl-but-3-ynyl]-carbamic acid tert-butyl ester (2.11 g, 99% yield) as an oil, which was used in the next step without further purification.

Workup

  1. extractionextracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-7d6dd87f4a3c4a8693b14218b843736c
Source dataset
uspto-grants-2013_12
Patent number
US08609660B2

Reaction notes

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