HCID 69591807, compound → HCID 58667143, compound

HRID 1793653Notes

Reaction equation

HRID 1793653 reaction equation
[Br:1][C:2]1[C:3]([C@@H:9]2[CH2:13][O:12][CH2:11][C@H:10]2[OH:14])=[C:4]([CH3:8])[S:5][C:6]=1[CH3:7]>C(OC=C)(=O)C>[Br:1][C:2]1[C:3]([C@H:9]2[CH2:13][O:12][CH2:11][C@@H:10]2[OH:14])=[C:4]([CH3:8])[S:5][C:6]=1[CH3:7]

Participants

3

Reactant 1

HCID 69591807HCID 69591807, compound

Product 1

HCID 58667143HCID 58667143, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 7904Vinyl AcetateSolvent

Procedure

Solid Novozym 435 is added to a solution of trans-4-(4-bromo-2,5-dimethyl-3-thienyl)tetrahydro-3-furanol (0.153 mol) in 425 ml of vinyl acetate and the mixture is subsequently stirred for 24 hours. The enzyme is removed by filtration and the residue is washed with tert-butyl methyl ether. After removal of the solvent, the two products are separated by means of chromatography. (3R,4S)-4-(Bromo-2,5-dimethyl-3-thienyl)tetrahydro-3-furanol is obtained in a yield of 49% (>99% ee) and (3S,4R)-4-(bromo-2,5-dimethyl-3-thienyl)tetrahydro-3-furanol acetate is obtained in a yield of 50% (>97% ee).

Workup

  1. customThe enzyme is removed by filtration
  2. washthe residue is washed with tert-butyl methyl ether
  3. customAfter removal of the solvent
  4. customthe two products are separated by means of chromatography

Sources & evidence

ORD record
ord-2e6d7b8a1d69492fbb66425e55f40318
Source dataset
uspto-grants-2006_07
Patent number
US07081533B2

Reaction notes

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