Dimethyl Sulfoxide → 7-(2-Formyl-6-oxo-piperidin-1-yl)-hept-5-ynoic acid methyl ester

HRID 2052895Notes

Reaction equation

CS(C)=O.[CH3:5][O:6][C:7](=[O:23])[CH2:8][CH2:9][CH2:10][C:11]#[C:12][CH2:13][N:14]1[C:19](=[O:20])[CH2:18][CH2:17][CH2:16][CH:15]1[CH2:21][OH:22].FC(F)(F)C([O-])=O.[NH+]1C=CC=CC=1>C1C=CC=CC=1>[CH3:5][O:6][C:7](=[O:23])[CH2:8][CH2:9][CH2:10][C:11]#[C:12][CH2:13][N:14]1[C:19](=[O:20])[CH2:18][CH2:17][CH2:16][CH:15]1[CH:21]=[O:22]

Participants

Conditions

Temperature: 0 °C

Procedure

1-(3-(Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 530 mg, 2.76 mmol) and DMSO (0.26 mL, 3.68 mmol) were added sequentially to a solution of 7-(2-hydroxymethyl-6-oxo-piperidin-1-yl)-hept-5-ynoic acid methyl ester (246 mg, 0.92 mmol) in benzene (7.0 mL) at rt. The mixture was cooled to 0° C. and pyridinium trifluoroacetate (196 mg, 1.01 mmol) was added. The reaction was allowed to warm to rt and then was stirred at rt for 2.5 h. The solution was decanted from the oily residue and the residue was washed with benzene (3×5 mL). The combined benzene phases were concentrated in vacuo to afford crude 7-(2-formyl-6-oxo-piperidin-1-yl)-hept-5-ynoic acid methyl ester that was used without further purification.

Workup

temperatureto warm to rt
customThe solution was decanted from the oily residue
washthe residue was washed with benzene (3×5 mL)
concentrationThe combined benzene phases were concentrated in vacuo

Sources & evidence

ORD record: ord-9e5add4e8a7f44c6b840081f708e96ef
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07326716B2

Reaction notes

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