Methyl iodide → HCID 23456169, compound

HRID 1680398Notes

Reaction equation

HRID 1680398 reaction equation
[C:1]1([N:7]2[C:11]([CH:12]=[O:13])=[C:10]3[C:14]([CH3:21])([C:19]#[N:20])[CH2:15][C:16]([CH3:18])([CH3:17])[C:9]3=[C:8]2[CH3:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Mn]([O-])(=O)(=O)=O.[K+].C1(N2C([C:40](O)=[O:41])=C3C(C)(C#N)CC(C)(C)C3=C2C)C=CC=CC=1.[H-].[Na+].CI>O.N1C=CC=CC=1>[C:1]1([N:7]2[C:11]([C:12]([O:41][CH3:40])=[O:13])=[C:10]3[C:14]([CH3:21])([C:19]#[N:20])[CH2:15][C:16]([CH3:17])([CH3:18])[C:9]3=[C:8]2[CH3:22])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516875Potassium PermanganateHCID 12607167HCID 12607167, compoundHCID 23456200HCID 23456200, compound

Product 1

HCID 23456169HCID 23456169, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Following a procedure similar to that described in Example 13C, 17.48 g. (0.06 mole) of 2-phenyl-3-formyl-2,4,5,6-tetrahydro-1,4,6,6-tetrmethylcyclopenta[c]pyrrole-4-carbonitrile was oxidized with 18.9 g. (0.12 mole) of potassium permanganate in 120 ml. of pyridine and 90 ml. of water to give 4.03 g. of 2-phenyl-3-carboxy-2,4,5,6-tetrahydro-1,4,6,6tetramethylcyclopenta[c]pyrrole-4-carbonitrile which was esterified by reaction of 9.83 g. (0.032 mole) of the acid with 1.713 g. (0.035 mole) of a 50% mineral oil dispersion of sodium hydride followed by 2.23 ml. (0.036 mole) of methyl iodide. There was thus obtained 4.18 of 2-phenyl-3-carbomethoxy-2,4,5,6-tetrahydro-1,4,6,6-tetramethylcyclopenta[c]pyrrole-4-carbonitrile.

Sources & evidence

ORD record
ord-239780a188fa45d1a823e32d10b97489
Source dataset
uspto-grants-1981_06
Patent number
US04273713

Reaction notes

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