Pyrrolidine → 7,8-dihydro-6,6-dimethyl-7-hydroxy-8-pyrrolidino-6H-pyrano [2,3-f] benzo-2,1,3-oxadiazole

HRID 1199415Notes

Reaction equation

HRID 1199415 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.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1>C(O)C>[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]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:3]1[OH:15])=[N:10][O:11][N:12]=3

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 98373347,8-dihydro-6,6-dimethyl-7,8-epoxy-6H-pyrano[2,3-f]benz-2,1,3-oxadiazole

Product 1

HCID 146739137,8-dihydro-6,6-dimethyl-7-hydroxy-8-pyrrolidino-6H-pyrano [2,3-f] benzo-2,1,3-oxadiazoleYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 150 mg (0.687 m mol) of 7,8-dihydro-6,6-dimethyl-7,8-epoxy-6H-pyrano [2,3-f] benzo-2,1,3-oxadiazole, 63 μl (0.756 m mol) of pyrrolidine and 2 ml of ethanol was refluxed with stirring for 31 hours. After the solvent was distilled off, the residue was subjected to a preparative silica gel thin layer chromatography using a developing solvent of ethyl acetate-methanol (1:1 (v/v)) to obtain 120 mg (yield: 60%) of the intended compound. A part of the obtained compound was dissolved in dry ether and added with HCl--EtOH to obtain hydrochloride of the intended compound as pale yellow crystals.

Workup

  1. temperaturewas refluxed
  2. distillationAfter the solvent was distilled off

Sources & evidence

ORD record
ord-22317fb98c1d4709b624dffea7cf5868
Source dataset
uspto-grants-1990_02
Patent number
US04900752

Reaction notes

Loading…