tert-Butyl 4-(2-((methanesulfonyl)oxy)ethyl)piperidine-1-carboxylate → 4-[2-(Furo[3,2-c]pyridin-2-ylmethoxy)ethyl]piperidine-1-carboxylic acid tert-butyl ester

HRID 217179

Reaction equation

CC([O-])(C)C.[K+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][O:22]S(C)(=O)=O)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[O:27]1[C:35]2[CH:34]=[CH:33][N:32]=[CH:31][C:30]=2[CH:29]=[C:28]1[CH2:36]O>C1COCC1>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][O:22][CH2:36][C:28]2[O:27][C:35]3[CH:34]=[CH:33][N:32]=[CH:31][C:30]=3[CH:29]=2)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

Conditions

Temperature: 20 °C

Procedure

t-BuOK (45 mg, 401 μmol) and 4-(2-methanesulfonyloxyethyl)piperidine-1-carboxylic acid tert-butyl ester (134 mg, 436 μmol) were added to a stirred solution of furo[3,2-c]pyridin-2-ylmethanol (Preparation 4, 50 mg, 336 μmol) in anhydrous THF (5 mL). The reaction was heated under reflux for 6 h, before being cooled to 20° C. and quenched with saturated aqueous NH4Cl. The mixture was extracted twice with EtOAc, then the combined organic extracts were washed with brine, dried (MgSO4), filtered, and concentrated. The residue was purified by column chromatography (EtOAc-MeOH, 1:0 to 50:1) to furnish the title compound: RT=2.86 min; m/z (ES+)=361.3 [M+H]+.

Workup

temperatureThe reaction was heated
temperatureunder reflux for 6 h
customquenched with saturated aqueous NH4Cl
extractionThe mixture was extracted twice with EtOAc
washthe combined organic extracts were washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography (EtOAc-MeOH, 1:0 to 50:1)

Sources & evidence

ORD record: ord-8cbc908f1a3b4e50bb93abe58c8043d2
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193359B2

Linked notes

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