Methyl iodide → (2RS,3SR)-3-(3-benzyloxyphenyl)-1-ethoxycarbonyl-3-methoxy-2-methylpyrrolidine

HRID 37565Notes

Reaction equation

HRID 37565 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](Br)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([O:18][C:19]([N:21]1[CH2:25][CH2:24][C:23](=[O:26])[CH:22]1[CH3:27])=[O:20])[CH3:17].[CH3:28]I>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:23]2([O:26][CH3:28])[CH2:24][CH2:25][N:21]([C:19]([O:18][CH2:16][CH3:17])=[O:20])[CH:22]2[CH3:27])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 27566381-(Benzyloxy)-3-bromobenzeneHCID 14664486Ethyl 2-methyl-3-oxopyrrolidine-1-carboxylate

Product 1

HCID 19935814(2RS,3SR)-3-(3-benzyloxyphenyl)-1-ethoxycarbonyl-3-methoxy-2-methylpyrrolidineYield 65%

Procedure

Using an analogous procedure to that described in the portion of Example 1 which is concerned with the preparation of starting materials, 3-benzyloxybromobenzene was reacted with 1-ethoxycarbonyl-2-methylpyrrolidin-3-one (J. Med. Pharm. Chem., 1962, 5, 755) and the resultant product was reacted with methyl iodide to give (2RS,3SR)-3-(3-benzyloxyphenyl)-1-ethoxycarbonyl-3-methoxy-2-methylpyrrolidine in 65% yield as an oil.

Sources & evidence

ORD record
ord-8debd797168d40c387acc85f5e642d3d
Source dataset
uspto-grants-1995_05
Patent number
US05420298

Reaction notes

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