Dimethyl Sulfoxide → [4-((R)-2-formyl-6-oxo-piperidin-1-yl)-butoxy]-acetic acid ethyl ester

HRID 349347Notes

Reaction equation

CS(C)=O.[CH2:5]([O:7][C:8](=[O:24])[CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:20](=[O:21])[CH2:19][CH2:18][CH2:17][C@@H:16]1[CH2:22][OH:23])[CH3:6].FC(F)(F)C([O-])=O.[NH+]1C=CC=CC=1>C1C=CC=CC=1>[CH2:5]([O:7][C:8](=[O:24])[CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:20](=[O:21])[CH2:19][CH2:18][CH2:17][C@@H:16]1[CH:22]=[O:23])[CH3:6]

Participants

Conditions

Temperature: 0 °C

Procedure

1-(3-(Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 505 mg, 2.63 mmol) and DMSO (0.25 mL, 3.52 mmol) were added sequentially to a solution of [4-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-butoxy]-acetic acid ethyl ester (252 mg, 0.88 mmol) in benzene (5 mL). The mixture was cooled to 0° C. and pyridinium trifluoroacetate (187 mg, 0.97 mmol) was added. The reaction was allowed to warm to rt and then was stirred at rt for 4.25 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 4-((R)-2-formyl-6-oxo-piperidin-1-yl)-butoxy]-acetic acid ethyl 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
customto afford crude 4-((R)-2-formyl-6-oxo-piperidin-1-yl)-butoxy]-acetic acid ethyl ester that
customwas used without further purification

Sources & evidence

ORD record: ord-3e63f515e683422f99e81903e048616c
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179820B2

Reaction notes

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