Sodium hydride → trans-3,4-dihydro-3-hydroxy-2,2-dimethyl-4-(3-oxo-1-cyclopent-1-enylamino)-2H-1-benzopyran-6-carbonitrile

HRID 1460614Notes

Reaction equation

HRID 1460614 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].[H-].[Na+].[NH2:25][C:26]1[CH2:30][CH2:29][C:28](=[O:31])[CH:27]=1>CS(C)=O>[OH:1][C@H:2]1[C@H:7]([NH:25][C:26]2[CH2:30][CH2:29][C:28](=[O:31])[CH:27]=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 122914403-Aminocyclopent-2-en-1-one

Product 1

HCID 14301304trans-3,4-dihydro-3-hydroxy-2,2-dimethyl-4-(3-oxo-1-cyclopent-1-enylamino)-2H-1-benzopyran-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.41 g of the epoxide of example 1 were solved in 36 ml of dimethylsulfoxide under a protective gas, and 360 mg of sodium hydrid were added. To this stirred suspension was added 1.71 g of 3-amino-cyclopent-2-en-1-one (Chem. Ber. 103, 2403 [1970]) in portions. After 21 hours, the reaction solution was worked up in an aqueous manner and extracted with ethyl acetate. The usual further processing and recrystallisation of the product obtained from ethyl acetate yielded white crystals having a m.p. of 174°-176° C.

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate
  3. customThe usual further processing and recrystallisation of the product
  4. customobtained from ethyl acetate yielded white crystals

Sources & evidence

ORD record
ord-bdeec7ddd59b45f7b4cd499d8abe20e0
Source dataset
uspto-grants-1991_12
Patent number
US05071871

Reaction notes

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