Azane;hydrate → (3R,4S)-4-amino-6-methoxy-2,2-dimethyl-7-nitro-3,4-dihydro-2H-1-benzopyran-3-ol

HRID 505642Notes

Reaction equation

[O:1]1[C@H:7]2[C@@H:2]1[C:3]([CH3:18])([CH3:17])[O:4][C:5]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9]([O:15][CH3:16])=[CH:8][C:6]=12.O.[NH3:20]>C(O)C>[NH2:20][C@H:7]1[C:6]2[CH:8]=[C:9]([O:15][CH3:16])[C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:5]=2[O:4][C:3]([CH3:18])([CH3:17])[C@@H:2]1[OH:1]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (3R*,4R*)-3,4-epoxy-6-methoxy-2,2-dimethyl-7-nitro-3,4-dihydro-2H-1-benzopyran (2.64 g, 10.5 mmol) in ethanol (26 mL), an ammonia water (26 mL) was added, and the resulting mixture was stirred in a sealed tube at 100° C. for 2 hours. Upon the completion of the reaction, the solvent was distilled off. An aqueous solution of saturated sodium carbonate was added to the residue, and the resulting mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and thereby the aimed product was obtained as red amorphous substance (yield: 84%).

Workup

customUpon the completion of the reaction
distillationthe solvent was distilled off
additionAn aqueous solution of saturated sodium carbonate was added to the residue
extractionthe resulting mixture was extracted with ethyl acetate
washThe organic phase was washed with saturated sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record: ord-0bb61f71ffe74a0184c35a136c2d5c84
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781483B2

Reaction notes

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