Potassium tert-butoxide → HCID 86677569, compound

HRID 2401112Notes

Reaction equation

HRID 2401112 reaction equation
C([O:3][C:4]([C:6]1([CH2:19][CH2:20][NH:21][C:22]2[C:23]([CH3:29])=[N:24][C:25]([Br:28])=[CH:26][CH:27]=2)[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=O)C.CC(C)([O-])C.[K+]>C1COCC1.C(OCC)(=O)C>[C:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][C:6]2([C:4](=[O:3])[N:21]([C:22]3[C:23]([CH3:29])=[N:24][C:25]([Br:28])=[CH:26][CH:27]=3)[CH2:20][CH2:19]2)[CH2:7][CH2:8]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86677568HCID 86677568, compound

Product 1

HCID 86677569HCID 86677569, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[2-(6-bromo-2-methyl-pyridin-3-ylamino)-ethyl]-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (0.44 g, 0.94 mmols) in THF (20 mL) was added a solution of potassium t-butoxide (1 M in THF) (2 mL), and allowed to stir at room temperature for 4 hours. The reaction mixture was then diluted with ethyl acetate (20 mL), quenched with water (5 mL). The aqueous layer was extracted with EtOAc (2×20 mL). The combined organics were washed with brine, and concentrated under vacuum to afford crude product. Purification on silica gel eluting with ethyl acetate in heptanes (0-75%) afforded 0.238 (60%) of title compound.

Workup

  1. customquenched with water (5 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (2×20 mL)
  3. washThe combined organics were washed with brine
  4. concentrationconcentrated under vacuum
  5. customto afford crude product
  6. customPurification on silica gel eluting with ethyl acetate in heptanes (0-75%)

Sources & evidence

ORD record
ord-13a1099eca1b44d7b5064eb2a2ef2ec6
Source dataset
uspto-grants-2014_08
Patent number
US08796278B2

Reaction notes

Loading…