Imidazole → 4(r)-Benzyl-3-(2-iodomethyl-3-methylbutyryl)oxazolidin-2-one

HRID 393698Notes

Reaction equation

HRID 393698 reaction equation
[I:1]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[CH2:27]([C@@H:34]1[CH2:38][O:37][C:36](=[O:39])[N:35]1[C:40](=[O:47])[C@@H:41]([CH2:45]O)[CH:42]([CH3:44])[CH3:43])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1(C)C=CC=CC=1>[CH2:27]([C@@H:34]1[CH2:38][O:37][C:36](=[O:39])[N:35]1[C:40](=[O:47])[CH:41]([CH2:45][I:1])[CH:42]([CH3:44])[CH3:43])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 228882854-(R)-Benzyl-3-(2-(R)-hydroxymethyl-3-methylbutyryl)oxazolidin-2one

Product 1

HCID 228882814(r)-Benzyl-3-(2-iodomethyl-3-methylbutyryl)oxazolidin-2-oneYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Iodine (42 g), triphenylphosphine (47 g) and imidazole (12 g) were added to a solution of 4-(R)-benzyl-3-(2-(R)-hydroxymethyl-3-methylbutyryl)oxazolidin-2-one (45 g) in toluene (400 ml) and the mixture was heated to 80° C. for 1 h, then cooled and washed with water and saturated brine. The solvent was dried (Na2SO4) and evaporated and the residue filtered through silica (200 g) eluting with diethyl ether-hexane 1:1 to give the title compound as a yellow viscous oil (56.4 g).

Workup

  1. temperaturecooled
  2. washwashed with water and saturated brine
  3. dry with materialThe solvent was dried (Na2SO4)
  4. customevaporated
  5. filtrationthe residue filtered through silica (200 g)
  6. washeluting with diethyl ether-hexane 1:1

Sources & evidence

ORD record
ord-6b771874e35349ca944fce93f84052ae
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

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