Alpha-D-Glucose → HCID 67995230, compound

HRID 2042938Notes

Reaction equation

HRID 2042938 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH2:2]1.O[C@H:16]1[O:24][C@H:23]([CH2:25][OH:26])[C@@H:21]([OH:22])[C@H:19]([OH:20])[C@H:17]1[OH:18]>CO>[OH:18][C@@H:17]1[C@@H:19]([OH:20])[C@H:21]([OH:22])[C@@H:23]([CH2:25][OH:26])[O:24][C@H:16]1[N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH2:2]1

Participants

4

Reactant 2

HCID 79025Alpha-D-GlucoseHCID 11816349Methyl 2-(2,3-dihydro-1H-indol-3-yl)acetate

Product 1

HCID 67995230HCID 67995230, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of indoline 75 (8.5 g, 44.2 mmol) in MeOH (150 mL) was added α-D-glucose (27 g, 146 mmol) at room temperature. The mixture was stirred at 70° C. for 60 h, cooled to room temperature and concentrated in vacuo to remove solvent. The residue was purified by silica column chromatography to provide the titled compound 76 (13.7 g, 88%). MH+354.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customto remove solvent
  4. customThe residue was purified by silica column chromatography

Sources & evidence

ORD record
ord-9a06d9b7ed3743de99c213af9790aea7
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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