Dabco → HCID 68877689, compound

HRID 2202808Notes

Reaction equation

HRID 2202808 reaction equation
C1N2CCN(CC2)C1.C([Li])CCC.[Cl:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=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].[Cl-].[NH4+]>C(OCC)C>[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][C:31]([OH:34])([C:16]2[C:15]([Cl:14])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

7

Reactant 5

HCID 9237DabcoHCID 122873-ChloropyridineHCID 25517Ammonium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 68877689HCID 68877689, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

DABCO (0.31 g, 2.75 mmol) in diethyl ether (11 mL) was cooled to −40° C., under nitrogen. n-Butyl lithium (2.5 M, 1.0 mL, 2.5 mmol) was added dropwise and stirred for 30 minutes. The temperature was decreased to −65° C., 3-chloropyridine (0.284 mL, 2.5 mmol) was slowly added and stirred for 30 minutes before a solution of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (0.5 g, 2.5 mmol) in diethyl ether (5 mL) was added for 30 minutes. Ammonium chloride was added and the mixture extracted into ethyl acetate, dried over sodium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 20% ethyl acetate/cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.18 g). LCMS m/z 313.3 [M+H]+. R.T.=4.51 min (Analytical Method 3).

Workup

  1. customwas decreased to −65° C.
  2. additionwas added for 30 minutes
  3. extractionthe mixture extracted into ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent removed by evaporation under vacuum
  7. customThe residue was purified by flash chromatography on silica eluting with 20% ethyl acetate/cyclohexane
  8. additionThe fractions containing the desired product
  9. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-2d80b5de0d1b45fc953e25d50606327d
Source dataset
uspto-grants-2016_06
Patent number
US09365564B2

Reaction notes

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