Sodium hydride → trans-3,4-dihydro-3-hydroxy-2,2-dimethyl-4-[N-methyl-N-(3-oxo-cyclopent-1-enyl)amino]-2H-1-benzopyran-6-carbonitrile

HRID 1460617Notes

Reaction equation

HRID 1460617 reaction equation
[OH:1][C@H:2]1[C@H:7](OC2CCC(=O)C=2)[C:6]2[CH:15]=[C:16]([C:19]#[N:20])[CH:17]=[CH:18][C:5]=2[O:4][C:3]1([CH3:22])[CH3:21].[CH3:23][NH:24][C:25]1[CH2:29][CH2:28][C:27](=[O:30])[CH:26]=1.[H-].[Na+]>CS(C)=O>[OH:1][C@H:2]1[C@H:7]([N:24]([CH3:23])[C:25]2[CH2:29][CH2:28][C:27](=[O:30])[CH:26]=2)[C:6]2[CH:15]=[C:16]([C:19]#[N:20])[CH:17]=[CH:18][C:5]=2[O:4][C:3]1([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 129348Sdz pco 400HCID 132179073-(Methylamino)cyclopent-2-en-1-one

Product 1

HCID 14301310trans-3,4-dihydro-3-hydroxy-2,2-dimethyl-4-[N-methyl-N-(3-oxo-cyclopent-1-enyl)amino]-2H-1-benzopyran-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4.02 g of the epoxide of example 1 are reacted analogously to example 5 with 2.44 g N-methyl-3-amino-cyclopent-2-en-1-on and 660 mg of sodium hydride (80%) in dimethylsulfoxide. Usual working up yields crystalls of the title compound having a m.p. of 271°-74° C.

Sources & evidence

ORD record
ord-92f61fe3a9de43a99da90180efff69fa
Source dataset
uspto-grants-1991_12
Patent number
US05071871

Reaction notes

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