Tetrahydrofuran → Tert-butyl 4-(5-phenyl-1,3,4-oxadiazol-2-yl)piperidine-1-carboxylate

HRID 222248Notes

Reaction equation

[C:1]([NH:9][NH:10][C:11]([CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.C1(C)C(S(Cl)(=O)=O)=CC=CC=1>C(N(CC)CC)C>[C:2]1([C:1]2[O:12][C:11]([CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)=[N:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of tert-butyl 4-[(2-benzoylhydrazino)carbonyl]piperidine-1-carboxylate (3.00 g) and THF (60 mL) were added triethylamine (7.2 mL) and toluenesulfonyl chloride (4.94 g), followed by stirring at 50° C. overnight. The reaction liquid was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20) to obtain tert-butyl 4-(5-phenyl-1,3,4-oxadiazol-2-yl)piperidine-1-carboxylate (2.84 g) as a colorless oily sub stance.

Workup

customThe reaction liquid
concentrationwas concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20)

Sources & evidence

ORD record: ord-583a514d5c4b4dd7af327b5a3d60ea85
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207199B2

Reaction notes

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