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

HRID 1281479Notes

Reaction equation

HRID 1281479 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-b4813161adfa40088af585cb40d6459f
Source dataset
uspto-grants-2002_09
Patent number
US06451814B1

Reaction notes

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