Tert-butyl 4-hydroxypiperidine-1-carboxylate → 1-(1-Tert-butoxycarbonylpiperidin-4-yl)-3-phenylpyrazole

HRID 222240Notes

Reaction equation

[C:1]1([C:7]2[CH:11]=[CH:10][NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[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.C(P(=CC#N)(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[C:1]1([C:7]2[CH:11]=[CH:10][N:9]([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:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-phenyl-1H-pyrazole (300 mg) in toluene (15 mL) were added tert-butyl 4-hydroxypiperidine-1-carboxylate (838 mg) and (tributylphosphoranylidene)acetonitrile (1.0 g), followed by stirring at 100° C. for 4 hours. The reaction liquid was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 to 50/50) and purified again by silica gel column chromatography (hexane/ethyl acetate=100/0 to 70/30) to obtain tert-butyl 4-(3-phenyl-1H-pyrazol-1-yl)piperidine-1-carboxylate (475 mg) as a colorless oily substance.

Workup

customThe reaction liquid
concentrationwas concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 to 50/50)
custompurified again by silica gel column chromatography (hexane/ethyl acetate=100/0 to 70/30)

Sources & evidence

ORD record: ord-1bb9cfa8fe244eb3a2aceaf65e188cb8
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207199B2

Reaction notes

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