Hexane → HCID 68003934, compound

HRID 1748530Notes

Reaction equation

HRID 1748530 reaction equation
CCCCCC.C([Li])CCC.Br[C:13]1[C:18]([CH3:19])=[CH:17][C:16]([Br:20])=[CH:15][N:14]=1.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][C:31](=[O:34])[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]>C1(C)C=CC=CC=1.O>[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][C:31]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([Br:20])=[CH:15][N:14]=2)([OH:34])[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

7

Reactant 4

HCID 8058HexaneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 8176802,5-Dibromo-3-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 68003934HCID 68003934, compoundYield 30.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

Under nitrogen atmosphere, 1.6M n-hexane solution of n-butyl lithium (65.6 ml) was added dropwise to a solution of 2,5-dibromo-3-picoline (25.1 g) in toluene (200 ml) at −78° C. and stirred at the same temperature for two hours. Next, a solution of 1-(tert-butoxycarbonyl)-4-piperidone (20.9 g) in toluene (200 ml) was added slowly dropwise. After the addition, the mixture was stirred at the same temperature for an hour. Then, the reaction solution was gradually warmed up to room temperature under stirring. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) and the product was solidified with n-hexane to give 4-(5-bromo-3-methylpyridin-2-yl)-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (11.4 g) as a white solid.

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred at the same temperature for an hour
  3. stirringunder stirring
  4. additionwas added
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-86919b3c38534aa9a29d48640ed0217f
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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