Lithium Hydroxide → HCID 66896845, compound

HRID 337688Notes

Reaction equation

HRID 337688 reaction equation
C1COCC1.[CH3:6][N:7]1[CH:12]=[C:11]([O:13][CH2:14][O:15][CH3:16])[C:10]([C@@H:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][C@H:18]2[C:30]([O:32]CC)=[O:31])=[CH:9][C:8]1=[O:35].[OH-].[Li+]>CO>[CH3:29][C:26]([O:25][C:23]([N:20]1[CH2:21][CH2:22][C@@H:17]([C:10]2[C:11]([O:13][CH2:14][O:15][CH3:16])=[CH:12][N:7]([CH3:6])[C:8](=[O:35])[CH:9]=2)[C@H:18]([C:30]([OH:32])=[O:31])[CH2:19]1)=[O:24])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 131732037HCID 131732037, compound

Product 1

HCID 66896845HCID 66896845, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 3:2 (v/v) THF:MeOH solution (0.04 M) of trans-1-(1,1-dimethylethyl) 3-ethyl 4-(1-methyl-5-{[(methyloxy)methyl]oxy}-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 eq.). The resulting cloudy solution was stirred vigorously at RT for 24 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 pink 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-16f21e95311540f6a78780d7700da3ad
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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