Reaction #632044

ord-7f8f05e9c5d24bcca0928593014d821c

Reaction equation

Fc1cccc2c1CCN2
4-fluoroindoline
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
D-glucose
CCO
ethyl alcohol
→
OC[C@H]1O[C@@H](N2CCc3c(F)cccc32)[C@H](O)[C@@H](O)[C@@H]1O
4-fluoro-1-(β-D-glucopyranosyl)indoline

Reactants

Fc1cccc2c1CCN2
4-fluoroindoline
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
D-glucose
CCO
ethyl alcohol

Reagents

None

Solvents

O
H2O

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturewas refluxed under argon atmosphere for 24 hours
  2. 2
    OtherThe solvent was evaporated under reduced pressure

Procedure

A mixture of 4-fluoroindoline (185 mg) and D-glucose (267 mg) in H2O (0.74 ml)-ethyl alcohol (9 ml) was refluxed under argon atmosphere for 24 hours. The solvent was evaporated under reduced pressure to give crude 4-fluoro-1-(β-D-glucopyranosyl)indoline, which was used in the subsequent step without further purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07935674B2uspto-grants-2011_05