Triacetoxyperiodinane → benzyl N-(1,1-dimethyl-3-oxo-propyl)carbamate

HRID 1056355Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:17])[NH:10][C:11]([CH3:16])([CH2:13][CH2:14][OH:15])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:17])[NH:10][C:11]([CH3:12])([CH2:13][CH:14]=[O:15])[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 100-mL round-bottomed flask was added benzyl(4-hydroxy-2-methylbutan-2-yl)carbamate (1.60 g, 6.74 mmol) and dess-martinperiodinane (24.72 mL, 7.42 mmol) (0.3 M in DCM, Sigma-Aldrich) at 0° C. The reaction was stirred at 0° C. for 40 min, then diluted with DCM (100 mL). The mixture was washed with sat. NaHCO3, and brine. The organic layer was dried (MgSO4), filtered and concentrated. The residue was purified via silica gel chromatography (eluted with 10-60% EtOAc in Hex) to give benzyl(2-methyl-4-oxobutan-2-yl)carbamate (1.04 g, 4.42 mmol, 65% yield) as a colorless oil. MS (ESI, pos. ion) m/z: 236.1 (M+1).

Workup

washThe mixture was washed with sat. NaHCO3, and brine
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified via silica gel chromatography (eluted with 10-60% EtOAc in Hex)

Sources & evidence

ORD record: ord-3308d5f181bd458eb3bf50b4b9b2967b
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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