Ethanol → tert-Butyl methylsulfonyl{3-[(2S)oxiranylmethoxy]phenyl}carbamate

HRID 395972Notes

Reaction equation

HRID 395972 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([N:15]([S:23]([CH3:26])(=[O:25])=[O:24])[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[CH:13][CH:14]=1)[C:2]1C=CC=C[CH:3]=1.C1CCCCC=1.C([OH:35])C>[Pd]>[CH3:26][S:23]([N:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C@@H:2]2[CH2:3][O:35]2)[CH:10]=1)[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:19])[CH3:20])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 702EthanolHCID 8079CyclohexeneHCID 53881295tert-Butyl 3-(benzyloxy)phenyl(methylsulfonyl)carbamate

Product 1

HCID 23381355tert-Butyl methylsulfonyl{3-[(2S)oxiranylmethoxy]phenyl}carbamate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

tert-Butyl 3-(benzyloxy)phenyl(methylsulfonyl)carbamate (2.6 g, 6.88 mmol) was dissolved in ethanol (25 mL), 10% palladium on carbon (0.75 g) and cyclohexene (1.5 mL) were added. The solution was heated to reflux for 3 hours. The solution was cooled and filtered through Celite. The solvent was removed in vacuo to yield crude title compound (1.93 g, 6.7 mmol).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 3 hours
  3. temperatureThe solution was cooled
  4. filtrationfiltered through Celite
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c70d56569ed949e9b3f243f7b859319a
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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