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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 444389Generated: October 31, 2026

Carbon Dioxide → 8a-Hydroxy-6-methoxy-1,5-dimethyl-8-methylidene-1,1a,2,8,8a,8b-hexahydroazireno[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione

https://huagongshe.com/reaction/444389

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCarbon DioxideHCID 280—
ReactantMitomycin BHCID 19973—
ReactantPotassium tert-butoxideHCID 23665647—
Solvent1,4-DioxaneHCID 31275—
Product8a-Hydroxy-6-methoxy-1,5-dimethyl-8-methylidene-1,1a,2,8,8a,8b-hexahydroazireno[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dioneHCID 17325017%

Reaction Steps

In this example, 100 mg of mitomycin B is dissolved in 5 ml of dioxane. To this solution, 100 mg of potassium t-butoxide is added and the mixture is stirred at room temperature for 2 days. The reaction mixture is then neutralized with an excess amount of dry ice and subjected to filtration. The filtrate is concentrated under reduced pressure and the residue is then subjected to silica gel column chromatography using a mixed solvent of acetone and chloroform (1:4) (volume ratio as is the same hereinafter) as a developer. Fractions of eluate which have a high Rf value and are blue are combined and concentrated under reduced pressure. The residue is crystallized from acetone and petroleum ether to obtain 14 mg of the desired compound (yield 17.0%) as purplish black needle-like crystals having the following physical properties.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04264504
Source datasetuspto-grants-1981_04
ORD IDord-8260773de63342a8b37ebc9d8e42b945
Source noteuspto-grants-1981_04