Lithium Hydroxide → HCID 66896405, compound

HRID 337678Notes

Reaction equation

HRID 337678 reaction equation
C1COCC1.[CH2:6]([N:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][C@H:15]2[C:27]([O:29]CC)=[O:28])=[CH:10][C:9]1=[O:32])[CH3:7].[OH-].[Li+]>CO>[CH3:24][C:23]([O:22][C:20]([N:17]1[CH2:18][CH2:19][C@@H:14]([C:11]2[CH:12]=[CH:13][N:8]([CH2:6][CH3:7])[C:9](=[O:32])[CH:10]=2)[C@H:15]([C:27]([OH:29])=[O:28])[CH2:16]1)=[O:21])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 131732027HCID 131732027, compound

Product 1

HCID 66896405HCID 66896405, 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-ethyl-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-e42535027d9a46b1b598115fc7fac88e
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

Loading…