Methyl iodide → [3-(1-Hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-7-yloxy)-propyl]-methyl-carbamic acid tert-butyl ester

HRID 1160065Notes

Reaction equation

HRID 1160065 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:24])[NH:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[C:19]2[B:20]([OH:23])[O:21][CH2:22][C:18]=2[CH:17]=[CH:16][CH:15]=1)([CH3:6])([CH3:5])[CH3:4].[CH3:25]I.[NH4+].[Cl-]>CN(C=O)C>[C:3]([O:7][C:8](=[O:24])[N:9]([CH2:10][CH2:11][CH2:12][O:13][C:14]1[C:19]2[B:20]([OH:23])[O:21][CH2:22][C:18]=2[CH:17]=[CH:16][CH:15]=1)[CH3:25])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 68645584[3-(1-Hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-7-yloxy)-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 68645741[3-(1-Hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-7-yloxy)-propyl]-methyl-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60% dispersion in mineral oil, 0.082 g, 2.05 mmol) was added portionwise to a solution of [3-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-7-yloxy)-propyl]-carbamic acid tert-butyl ester (0.212 g, 0.690 mmol) and MeI (1.03 mL, 2.07 mmol) in anhydrous DMF (5 mL) at 0° C. The reaction was then stirred at rt for 2 h. The mixture was cooled to 0° C., acidified to pH 6 using a sat. NH4Cl, and then extracted with EtOAc. The organic fractions were dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (40% EtOAc/hexane) to give the title compound as a colorless oil: yield 0.17 g (77%).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionextracted with EtOAc
  3. dry with materialThe organic fractions were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (40% EtOAc/hexane)

Sources & evidence

ORD record
ord-e72d5810d5c34ed8b19a882e41fd284f
Source dataset
uspto-grants-2010_10
Patent number
US07816344B2

Reaction notes

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