Methyl iodide → (1SR,3RS,4SR)-3-cyano-4-methoxy-cyclopentanecarboxylic acid methyl ester

HRID 2244695Notes

Reaction equation

[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([OH:10])[CH:7]([C:11]#[N:12])[CH2:6]1)=[O:4].[CH3:13]I>C1COCC1>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([O:10][CH3:13])[CH:7]([C:11]#[N:12])[CH2:6]1)=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of (1SR,3RS,4SR)-3-cyano-4-hydroxy-cyclopentanecarboxylic acid methyl ester (878 mg; example 15A) in THF (15 ml) was transferred to a sealed tube and treated with Ag2O (3.6 g) and methyl iodide (3.23 ml) and stirred at 60° C. overnight. The reaction mixture was filtered, and the cake was rinsed with plenty of THF. The filtrate was concentrated. The crude product was purified by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 65:35) to give (1SR,3RS,4SR)-3-cyano-4-methoxy-cyclopentanecarboxylic acid methyl ester (600 mg) as light yellow oil.

Workup

filtrationThe reaction mixture was filtered
washthe cake was rinsed with plenty of THF
concentrationThe filtrate was concentrated
customThe crude product was purified by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 65:35)

Sources & evidence

ORD record: ord-0a7b556cfdc34e6f85ae4435ca046022
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678917B2

Reaction notes

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