Sodium ethoxide → HCID 131732035, compound

HRID 337686Notes

Reaction equation

HRID 337686 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[C@H:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][C@H:12]1[C:24]([O:26][CH2:27][CH3:28])=[O:25].[O-]CC.[Na+]>C(O)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[C@@H:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])[CH2:13][C@H:12]1[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 131732034HCID 131732034, compound

Product 1

HCID 131732035HCID 131732035, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

To an ethanol solution (0.1 M) of cis-1-(1,1-dimethylethyl) 3-ethyl 4-(3-{[(methyloxy)methyl]oxy}-4-pyridinyl)-1,3-piperidinedicarboxylate (1 eq.) from the previous step was added freshly prepared sodium ethoxide (1.2 eq.). The resulting yellow-orange solution was heated at 55° C. for 16 h. The volatiles were then removed in vacuo and the residue was partitioned between EtOAc and sat. aq. NH4Cl. The aqueous layer was separated and back-extracted with EtOAc. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of column chromatography (SiO2, 95:5 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc) afforded the title compound as a pale yellow oil.

Workup

  1. customThe volatiles were then removed in vacuo
  2. customthe residue was partitioned between EtOAc and sat. aq. NH4Cl
  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
  8. concentrationthe filtrate concentrated in vacuo
  9. customPurification of the crude product
  10. customthus obtained by way of column chromatography (SiO2, 95:5 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-b9e72903077d43998452d7b6475c3250
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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