Pyrrolidine → HCID 69949854, compound

HRID 1108220Notes

Reaction equation

HRID 1108220 reaction equation
[C:1]([NH:9][C:10]1[C:11]([N+:23]([O-:25])=[O:24])=[CH:12][C:13]2[O:18][C:17]([CH3:20])([CH3:19])[CH:16]3[O:21][CH:15]3[C:14]=2[CH:22]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>C(O)C>[C:1]([NH:9][C:10]1[C:11]([N+:23]([O-:25])=[O:24])=[CH:12][C:13]2[O:18][C:17]([CH3:20])([CH3:19])[C@@H:16]([OH:21])[C@H:15]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[C:14]=2[CH:22]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 15453740HCID 15453740, compound

Product 1

HCID 69949854HCID 69949854, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of an ethanol (5 mL) solution of a 6-(benzoylamino)-3,4-epoxy-3,4-dihydro-2,2-dimethyl-7-nitro-2H-1-benzopyran (II-1) (147 mg, 0.43 mmol) was added with a pyrrolidine (0.07 mL) and heated under reflux for two hours. After the mixture was cooled to room temperature, the mixture was concentrated and the obtained residue was purified through silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain the intended product (40.3 mg, 23%) as a brown solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for two hours
  3. concentrationthe mixture was concentrated
  4. customthe obtained residue was purified through silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-085ca6250410493c9dbccdcaf9467478
Source dataset
uspto-grants-2000_05
Patent number
US06066631

Reaction notes

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