2-Pyrrolidone → Rilmakalim

HRID 2379786Notes

Reaction equation

HRID 2379786 reaction equation
[CH3:1][C:2]1([CH3:22])[O:7][C:6]2[CH:8]=[CH:9][C:10]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])=[CH:11][C:5]=2[CH:4]2[O:21][CH:3]12.[H-].[Na+].[NH:25]1[CH2:29][CH2:28][CH2:27][C:26]1=[O:30]>CS(C)=O>[CH3:22][C:2]1([CH3:1])[O:7][C:6]2[CH:8]=[CH:9][C:10]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:13])=[O:14])=[CH:11][C:5]=2[C@@H:4]([N:25]2[CH2:29][CH2:28][CH2:27][C:26]2=[O:30])[C@@H:3]1[OH:21]

Participants

5

Reactant 3

HCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 14517463HCID 14517463, compound

Product 1

HCID 65966Rilmakalim

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 6.3 g (0.02 mole) of 3,4-dihydro-2,2-di-methyl-3,4-epoxy-6-phenylsulfonyl-2H-benzo[b]pyran in 20 ml of DMSO is added dropwise, at 20°, to a suspension of 0.6 g (0.02 mole) of 80% NaH in 10 ml of DMSO. Then 2.3 ml (0.03 mole) of 2-pyrrolidinone are added, and the mixture is stirred at 45° for one hour. After it has stood at 20° overnight it is introduced into ice-water. The precipitate is filtered off with suction, washed to neutrality, dried and chromatographed on silica gel with methylene chloride/methanol 19:1. 30 ml fractions are collected. Fractions 12-22 are concentrated, and the residue is recrystallized from acetonitrile.

Workup

  1. waitAfter it has stood at 20° overnight
  2. filtrationThe precipitate is filtered off with suction
  3. washwashed to neutrality
  4. customdried
  5. customchromatographed on silica gel with methylene chloride/methanol 19:1
  6. custom30 ml fractions are collected
  7. concentrationFractions 12-22 are concentrated
  8. customthe residue is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-c96697f760454004aa57fcb2c374a4b7
Source dataset
uspto-grants-1994_11
Patent number
US05364878

Reaction notes

Loading…