Potassium tert-butoxide → HCID 67315804, compound

HRID 2059919Notes

Reaction equation

HRID 2059919 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:20][CH2:21][C:22](OC)=[O:23])([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC([O-])(C)C.[K+]>C1COCC1>[O:23]=[C:22]1[CH2:21][CH2:20][C:11]2([CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:12]2)[CH2:14][CH:15]1[C:16]([O:18][CH3:19])=[O:17]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86641304HCID 86641304, compound

Product 1

HCID 67315804HCID 67315804, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dimethyl 3,3′-(1-(tert-butoxycarbonyl)piperidine-4,4-diyl)dipropanoate (600 mg, 1.68 mmol) was dissolved in dry THF (10 ml) and a solution of t-BuOK (417 mg, 3.6 mmol) in THF was added at ice cold reaction conditions. The reaction mixture was stirred at room temperature for 2 h. TLC revealed completion of the reaction. The solvent was evaporated to dryness, the residue diluted with ethyl acetate and washed with water and brine. The organic layer was dried over Na2SO4, concentrated to dryness and purified by column chromatography to obtain the desired compound. Yield: 78%

Workup

  1. customcompletion of the reaction
  2. customThe solvent was evaporated to dryness
  3. additionthe residue diluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated to dryness
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-1bacfae85dca4f8eab36f9ae392dc763
Source dataset
uspto-grants-2012_10
Patent number
US08278319B2

Reaction notes

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