Triacetoxyperiodinane → Tert-butyl (5-methoxy-2-(3-methyl-2-oxobutyl)phenyl)carbamate

HRID 2409989Notes

Reaction equation

HRID 2409989 reaction equation
[OH:1][CH:2]([CH:20]([CH3:22])[CH3:21])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][C:2](=[O:1])[CH:20]([CH3:21])[CH3:22])=[C:5]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:6]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86703306tert-Butyl [2-(2-hydroxy-3-methylbutyl)-5-methoxyphenyl]carbamate

Product 1

HCID 69096724Tert-butyl (5-methoxy-2-(3-methyl-2-oxobutyl)phenyl)carbamateYield 94.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [2-(2-hydroxy-3-methylbutyl)-5-methoxyphenyl]-carbamate (100 mg) in dichloromethane (1.5 mL) was added Dess-Martin periodinane (164 mg), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was filtrated through Celite (registered trademark), and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (94 mg). 1H-NMR (CDCl3) δ ppm: 1.13 (6H, d, J=7.0 Hz), 1.52 (9H, s), 2.72-2.86 (1H, m), 3.66 (2H, s), 3.80 (3H, s), 6.59 (1H, dd, J=2.6, 8.5 Hz), 7.02 (1H, d, J=8.5 Hz), 7.47 (1H, br s), 7.60-7.90 (1H, br).

Workup

  1. filtrationThe reaction mixture was filtrated through Celite (registered trademark)
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-9a1e83f0f3b84ab2bd0f1e8a9a121be8
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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