Lithium Hydroxide → HCID 66896075, compound

HRID 337672Notes

Reaction equation

HRID 337672 reaction equation
C1COCC1.[CH3:6][N:7]1[CH:12]=[CH:11][C:10]([C@@H:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][C@H:14]2[C:26]([O:28]CC)=[O:27])=[CH:9][C:8]1=[O:31].[OH-].[Li+]>CO>[CH3:25][C:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][C@@H:13]([C:10]2[CH:11]=[CH:12][N:7]([CH3:6])[C:8](=[O:31])[CH:9]=2)[C@H:14]([C:26]([OH:28])=[O:27])[CH2:15]1)=[O:20])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 131732022HCID 131732022, compound

Product 1

HCID 66896075HCID 66896075, 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-methyl-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-86c2ac6d28be433183b6e78d430a1fa7
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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