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

HRID 1199410Notes

Reaction equation

HRID 1199410 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.CCO.[NH3:20]>>[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]([NH2:20])[CH:3]1[OH:15])=[N:10][O:11][N:12]=3

Participants

4

Reactant 3

HCID 222AmmoniaHCID 702EthanolHCID 98373347,8-dihydro-6,6-dimethyl-7,8-epoxy-6H-pyrano[2,3-f]benz-2,1,3-oxadiazole

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

Workup

  1. distillationThe reaction solution was distilled off

Sources & evidence

ORD record
ord-d5d4330c6233416ebf391f441ac31d1e
Source dataset
uspto-grants-1990_02
Patent number
US04900752

Reaction notes

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