Ammonium Chloride → HCID 118075677, compound

HRID 1051590Notes

Reaction equation

C([Li])CCC.[Br:6][C:7]1[C:11](Br)=[N:10][N:9]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[N:8]=1.BrC1N=NN(C2CCN(C(OC(C)(C)C)=O)CC2)C=1Br.[Cl-].[NH4+]>O1CCCC1>[Br:6][C:7]1[CH:11]=[N:10][N:9]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[N:8]=1

Participants

Conditions

Temperature: -78 °C

Procedure

n-Butyllithium (2.5 M in hexanes, 2.92 mL, 7.30 mmol) was added dropwise to a −78° C. solution containing a mixture of tert-butyl 4-(4,5-dibromo-2H-1,2,3-triazol-2-yl)piperidine-1-carboxylate and tert-butyl 4-(4,5-dibromo-1H-1,2,3-triazol-1-yl)piperidine-1-carboxylate (3.00 g, 7.35 mmol) in tetrahydrofuran (20 mL). The resulting solution stirred for 1 hour at −78° C., and then the reaction mixture was poured into saturated aqueous ammonium chloride solution (20 mL). The aqueous phase was separated and extracted with ethyl acetate (3×20 mL), and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 2:1, ethyl acetate/petroleum ether) to afford tert-butyl 4-(4-bromo-2H-1,2,3-triazol-2-yl)piperidine-1-carboxylate (0. 800 g, 33%) as a colorless oil. MS (ESI, pos. ion) m/z 331, 333 [M+H]+.

Workup

additioncontaining
customThe aqueous phase was separated
extractionextracted with ethyl acetate (3×20 mL)
dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under vacuum
customThe residue was purified via column chromatography on silica gel (eluting with 2:1, ethyl acetate/petroleum ether)

Sources & evidence

ORD record: ord-387aa2bbd50a4851a95580708c6db232
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388161B2

Reaction notes

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