Ethanol → 4-fluoro-1-(beta-D-glucopyranosyl)indoline

HRID 544862Notes

Reaction equation

HRID 544862 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][NH:6]2.[O:11]=[CH:12][C@@H:13]([C@H:15]([C@@H:17]([C@@H:19]([CH2:21][OH:22])[OH:20])[OH:18])[OH:16])O.C(O)C>O>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][N:6]2[C@@H:21]1[O:22][C@H:13]([CH2:12][OH:11])[C@@H:15]([OH:16])[C@H:17]([OH:18])[C@H:19]1[OH:20]

Participants

5

Reactant 3

HCID 702EthanolHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 162444404-Fluoro-2,3-dihydro-1H-indole

Product 1

HCID 670203834-fluoro-1-(beta-D-glucopyranosyl)indoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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.

Workup

  1. temperaturewas refluxed under argon atmosphere for 24 hours
  2. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7f8f05e9c5d24bcca0928593014d821c
Source dataset
uspto-grants-2011_05
Patent number
US07935674B2

Reaction notes

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