Sodium hydride → (+)-trans-4-[8-(2-Hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-4-oxo-4h-chromen-2-yl]-benzonitrile

HRID 1363362Notes

Reaction equation

HRID 1363362 reaction equation
[OH:1][C:2]1[C:7]([C@@H:8]2[CH2:12][CH2:11][N:10]([CH3:13])[C@H:9]2[CH2:14][OH:15])=[C:6]([O:16][CH3:17])[CH:5]=[C:4]([O:18][CH3:19])[C:3]=1[C:20](=[O:22])[CH3:21].[C:23]([C:25]1[CH:34]=[CH:33][C:28]([C:29](OC)=O)=[CH:27][CH:26]=1)#[N:24].[H-].[Na+]>CN(C=O)C>[OH:15][CH2:14][C@H:9]1[C@H:8]([C:7]2[C:6]([O:16][CH3:17])=[CH:5][C:4]([O:18][CH3:19])=[C:3]3[C:2]=2[O:1][C:29]([C:28]2[CH:33]=[CH:34][C:25]([C:23]#[N:24])=[CH:26][CH:27]=2)=[CH:21][C:20]3=[O:22])[CH2:12][CH2:11][N:10]1[CH3:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 70791Methyl 4-cyanobenzoateHCID 59318484(-)-trans-1-[2-Hydroxy-3-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-4,6-dimethoxyphenyl]-1-ethanone

Product 1

HCID 66933662(+)-trans-4-[8-(2-Hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-4-oxo-4h-chromen-2-yl]-benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound of example 6 (1.5 g, 4.85 mmol) in dry DMF (15 mL) reacted with methyl 4-cyanobenzoate (2.57 g, 17.2 mmol) in the presence of NaH (50%, 1.2 g, 25 mmol), as described example 16, afforded the title compound.

Sources & evidence

ORD record
ord-90dfccb49e1d4390b91c0e2aca7fe591
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

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