Acetic Acid → HCID 117667469, compound

HRID 1526197Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:8]=1)([O-:3])=[O:2].C(O[C:18]1(O[Si](C)(C)C)[CH2:20][CH2:19]1)C.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH:18]1([N:12]2[CH2:13][CH2:14][CH:9]([N:7]3[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[N:6]3)[CH2:10][CH2:11]2)[CH2:20][CH2:19]1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 4-(4-nitro-1H-pyrazol-1-yl)piperidine (100 mg), (1-ethoxycyclopropoxy) trimethylsilane (267 mg), acetic acid (292 μL), Molecular Sieve 3 A (100 mg), and sodium cyanoborohydride (96 mg), and methanol (3 mL) was stirred at 65° C. for 8 hours. After leaving to be cooled, the insoluble matter was separated by filtration and the filtrate was concentrated. The residue was dissolved in ethyl acetate, washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=100:0-95:5) to obtain 1-cyclopropyl-4-(4-nitro-1H-pyrazol-1-yl)piperidine (110 mg) as a colorless solid.

Workup

customAfter leaving
temperatureto be cooled
customthe insoluble matter was separated by filtration
concentrationthe filtrate was concentrated
dissolutionThe residue was dissolved in ethyl acetate
washwashed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=100:0-95:5)

Sources & evidence

ORD record: ord-c3cb00c87ad7456d8f35209c782ca2cc
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085540B2

Reaction notes

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