Lithium Hydroxide → HCID 67062032, compound

HRID 337683Notes

Reaction equation

HRID 337683 reaction equation
C1COCC1.[CH3:6][N:7]1[C:12]([CH3:13])=[C:11]([CH3:14])[C:10]([C@@H:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][C@H:16]2[C:28]([O:30]CC)=[O:29])=[CH:9][C:8]1=[O:33].[OH-].[Li+]>CO>[CH3:27][C:24]([O:23][C:21]([N:18]1[CH2:19][CH2:20][C@@H:15]([C:10]2[C:11]([CH3:14])=[C:12]([CH3:13])[N:7]([CH3:6])[C:8](=[O:33])[CH:9]=2)[C@H:16]([C:28]([OH:30])=[O:29])[CH2:17]1)=[O:22])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 131732032HCID 131732032, compound

Product 1

HCID 67062032HCID 67062032, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 3:2 (v/v) THF:MeOH solution (0.07 M) of trans-1-(1,1-dimethylethyl) 3-ethyl 4-(1,5,6-trimethyl-2-oxo-1,2-dihydro-4-pyridinyl)-1,3-piperidinedicarboxylate (1 eq.) from the previous step was added lithium hydroxide (1 M aq. solution, 3.1 eq.). The resulting cloudy solution was stirred vigorously at RT for 18 h. The volatiles were then removed in vacuo and the residue was partitioned between EtOAc and 10% aq. HCl. The aqueous layer was separated and back-extracted with EtOAc. The combined organic extracts were washed further with water and brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a white solid.

Workup

  1. customThe volatiles were then removed in vacuo
  2. customthe residue was partitioned between EtOAc and 10% aq. HCl
  3. customThe aqueous layer was separated
  4. extractionback-extracted with EtOAc
  5. washThe combined organic extracts were washed further with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-255457caf3e54dd080c8501d7a2e9fd7
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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