Triacetoxyperiodinane → HCID 57514175, compound

HRID 1912450Notes

Reaction equation

HRID 1912450 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28](=[O:41])[NH:29][C:30]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([Br:40])[CH:35]=1)([CH3:33])[CH2:31][OH:32])([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[C:23]([O:27][C:28](=[O:41])[NH:29][C:30]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([Br:40])[CH:35]=1)([CH3:33])[CH:31]=[O:32])([CH3:24])([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57514173HCID 57514173, compound

Product 1

HCID 57514175HCID 57514175, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dess-Martin periodinane (3.55 g, 8.36 mmol) was added portionwise over 5 minutes to a solution of rac-[1-(3-bromo-phenyl)-2-hydroxy-1-methyl-ethyl]-carbamic acid tert-butyl ester (2.3 g, 6.97 mmol) in dry DCM (45 mL) at 0° C. The mixture was stirred at 0° C. for 10 minutes and at room temperature for 1 hour. The reaction mixture was quenched with NaHCO3 (aq. sat. solution) followed by NaHSO3 (aq. sat. solution). Then Et2O was added and the mixture was stirred at room temperature for 30 minutes. The organic layer was separated and the aqueous layer was further extracted with Et2O. The combined organic layers were separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; DCM). The desired fractions were collected and concentrated in vacuo to yield rac-[1-(3-bromo-phenyl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester (2 g, 88% yield) as a colourless oil.

Workup

  1. customThe reaction mixture was quenched with NaHCO3 (aq. sat. solution)
  2. additionThen Et2O was added
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was further extracted with Et2O
  6. customThe combined organic layers were separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvents evaporated in vacuo
  10. customThe crude product was purified by flash column chromatography (silica gel; DCM)
  11. customThe desired fractions were collected
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3bdb208316b542aab5ed261ec614091c
Source dataset
uspto-grants-2013_12
Patent number
US08609660B2

Reaction notes

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