Triacetoxyperiodinane → [5-Methoxy-2-(2-oxo-butyl)-phenyl]-carbamic acid t-butyl Ester

HRID 1825158Notes

Reaction equation

HRID 1825158 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28](=[O:43])[NH:29][C:30]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:31]=1[CH2:38][CH:39]([OH:42])[CH2:40][CH3:41])([CH3:26])([CH3:25])[CH3:24]>C1COCC1>[C:23]([O:27][C:28](=[O:43])[NH:29][C:30]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:31]=1[CH2:38][C:39](=[O:42])[CH2:40][CH3:41])([CH3:25])([CH3:24])[CH3:26]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 20767944[2-(2-Hydroxy-butyl)-5-methoxy-phenyl]-carbamic acid t-butyl Ester

Product 1

HCID 20767945[5-Methoxy-2-(2-oxo-butyl)-phenyl]-carbamic acid t-butyl EsterYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Dess-Martin reagent (2.82 g, 6.68 mmole) in 80 ml THF cooled at 0° C. was added [2-(2-hydroxy-butyl)-5-methoxy-phenyl]-carbamic acid t-butyl ester 73a (1.64 g, 5.57 mmole) in 20 ml THF. The reaction mixture was stirred and warmed to room temperature for 2 h, quenched with half saturated NaHCO3, extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The residue was purified by flash column chromatography (10–15% EtOAc in hexane) to give colorless oil (1.36 g, 84%). 1H NMR (CDCl3) δ 7.67 (1H, bs), 7.48 (1H, s), 6.99–7.03 (1H, m), 6.56–6.60 (1H, m), 3.79 (3H, s), 3.59 (2H, s), 2.53–2.61 (2H, q, J=7.2 Hz), 1.51 (9H, s), 1.02 (3H, t, J=7.2 Hz). ESIMS (MNa+): 316.10.

Workup

  1. customquenched with half saturated NaHCO3
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (10–15% EtOAc in hexane)

Sources & evidence

ORD record
ord-506079f8626541f9b3bbb4645bf8b029
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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