7,8-dihydro-6,6-dimethyl-7,8-epoxy-6H-pyrano[2,3-f]benz-2,1,3-oxadiazole → (+)-7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano[2,3-f]benz-2,1,3-oxadiazole

HRID 581022Notes

Reaction equation

HRID 581022 reaction equation
[CH3:1][C:2]1([CH3:16])[O:14][C:6]2=[CH:7][C:8]3[C:9]([CH:13]=[C:5]2[CH:4]2[O:15][CH:3]12)=[N:10][O:11][N:12]=3.[NH3:17].CCO>>[CH3:1][C:2]1([CH3:16])[O:14][C:6]2=[CH:7][C:8]3[C:9]([CH:13]=[C:5]2[CH:4]([NH2:17])[CH:3]1[OH:15])=[N:10][O:11][N:12]=3

Participants

3

Reactant 2

HCID 98373347,8-dihydro-6,6-dimethyl-7,8-epoxy-6H-pyrano[2,3-f]benz-2,1,3-oxadiazoleHCID 22020343Ethanol, reaction products with ammonia, distn. residues

Product 1

HCID 11107308(+)-7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano[2,3-f]benz-2,1,3-oxadiazoleYield 87%

Procedure

0.82 g (3.8 mmol) of 7,8-dihydro-6,6-dimethyl-7,8-epoxy-6H-pyrano[2,3-f]benzo-2,1,3-oxadiazole were dissolved in 25 ml of 16.7% NH3 -EtOH and reacted for at 60° C. for 48 hours in a pressure glass tube. The solvent was distilled off, and the residue was subjected to silica gel column chromatography (eluent: ethyl acetate-methanol=5:1) to obtain 0.77 g of the intended compound as a brown solid. (yield: 87%) A part of the product was recrystallized from ethanol to obtain pure colorless crystals of the intended compound.

Workup

  1. customreacted for at 60° C. for 48 hours in a pressure glass tube
  2. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-10c4bc997de94b79a9303bccfef834bd
Source dataset
uspto-grants-1999_07
Patent number
US05919806

Reaction notes

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