Dimethylformamide → 3(S)-Azido-6(R)-phenylperhydroazepin-2-one

HRID 569754Notes

Reaction equation

[N-:1]=[N+:2]=[N-:3].[Na+].CN(C)C=O.Br[CH:11]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][NH:13][C:12]1=[O:24]>C(OCC)(=O)C>[N:1]([C@@H:11]1[CH2:17][CH2:16][C@@H:15]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:14][NH:13][C:12]1=[O:24])=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 60 °C

Procedure

2.0 g of sodium azide were added to 20 ml of dimethylformamide containing 1.6 g of 3-bromo-6-phenylperhydroazepin-2-one (Isomer A) [prepared as described in step (e) above]. The mixture was stirred for 6 hours at 60° C. and then diluted with ethyl acetate, washed with water three times and dried over anhydrous magnesium sulfate. The solvent was then distilled off. The crystalline residue was triturated in a 1:1 by volume mixture of methylene chloride and diisopropyl ether and then collected by filtration, to give 1.14 g of the title compound melting at 150°-152° C. (with decomposition).

Workup

custom[prepared as described in step (e) above]
washwashed with water three times
dry with materialdried over anhydrous magnesium sulfate
distillationThe solvent was then distilled off
customThe crystalline residue was triturated in a 1:1 by volume mixture of methylene chloride and diisopropyl ether
filtrationcollected by filtration

Sources & evidence

ORD record: ord-16ad80cb1eef4f9c8a7b6958ec7980db
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04734410

Reaction notes

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