Dimethyl Sulfoxide → [4-((R)-2-formyl-6-oxo-piperidin-1-yl)-but-2-ynyloxy]-acetonitrile

HRID 349372Notes

Reaction equation

CCN=C=NCCCN(C)C.[OH:12][CH2:13][C@H:14]1[CH2:19][CH2:18][CH2:17][C:16](=[O:20])[N:15]1[CH2:21][C:22]#[C:23][CH2:24][O:25][CH2:26][C:27]#[N:28].CS(C)=O.FC(F)(F)C([O-])=O.[NH+]1C=CC=CC=1>C1C=CC=CC=1>[CH:13]([C@H:14]1[CH2:19][CH2:18][CH2:17][C:16](=[O:20])[N:15]1[CH2:21][C:22]#[C:23][CH2:24][O:25][CH2:26][C:27]#[N:28])=[O:12]

Participants

Conditions

Temperature: 0 °C

Procedure

EDCI (288 mg, 1.50 mmol) was added to a solution of [4-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-but-2-ynyloxy]-acetonitrile (118 mg, 0.50 mmol) in benzene (4 mL). The reaction mixture was cooled to 0° C. and DMSO (0.14 mL, 2.0 mmol) was added. After 5 min at 0° C., pyridinium trifluoroacetate (106 mg, 0.55 mmol) was added. The reaction was allowed to warm to rt and then was stirred at rt for 3 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)-but-2-ynyloxy]-acetonitrile, which 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-0fba23b5828944799ebc5e2bb115f663
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179820B2

Reaction notes

Loading…