tert-butyl 4-(4,5-dibromo-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate → tert-Butyl 4-(4-bromo-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

HRID 1685165Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:21][CH2:22][O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[C:16](Br)=[C:17]([Br:19])[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[N:15]([CH2:21][CH2:22][O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[CH:16]=[C:17]([Br:19])[N:18]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: -78 °C

Procedure

Add 4-{4,5-dibromo-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-imidazol-2-yl}-piperidine-1-carboxylic acid tert-butyl ester (39.0 g; 0.073 mol; 1.0 equiv) to THF (600 mL) and cool to −78° C. under an argon atmosphere. Add n-BuLi solution (1.6 M in cyclohexane) (53.7 mL; 0.087 mol; 1.2 equiv) drop-wise in 1 h and allow to come to −30° C. in 2 h. Quench the reaction with saturated ammonium chloride solution and extract with EA. Evaporate the organic layer and purify the residue with silica gel chromatography to give the title compound (13.2 g; 39%).

Workup

customQuench
customthe reaction with saturated ammonium chloride solution
extractionextract with EA
customEvaporate the organic layer
custompurify the residue with silica gel chromatography

Sources & evidence

ORD record: ord-6c20bd664cda47518adef96a5f5669ee
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148387B2

Reaction notes

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