2-Bromopyridine → tert-Butyl 4-[hydroxy(pyridin-2-yl)methyl]piperidine-1-carboxylate

HRID 335149Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[CH:13]([CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)=[O:14]>C1COCC1>[OH:14][CH:13]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)[CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1

Participants

Conditions

Temperature: -78 °C

Procedure

Placed 2-bromopyridine (0.833 g, 5.27 mmol) in THF (25 mL) and cooled to −78° C. Butyllithium (2.11 mL, 5.27 mmol) was slowly added and stirred for 5 minutes. Dissolved tert-butyl 4-formylpiperidine-1-carboxylate (0.500 g, 2.34 mmol) in THF (3 mL) and added slowly to the above solution then stirred at −78° C. for 30 minutes. Added ammonium chloride and extracted with CH2Cl2. Concentrated and purified by silica gel to give the title compound (0.229 g, 33.4% yield)

Workup

stirringthen stirred at −78° C. for 30 minutes
extractionAdded ammonium chloride and extracted with CH2Cl2
concentrationConcentrated
custompurified by silica gel

Sources & evidence

ORD record: ord-edd926cdec824facb61cb63a39f242c2
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883828B2

Reaction notes

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