Acetic Acid → HCID 21955351, compound

HRID 747006Notes

Reaction equation

HRID 747006 reaction equation
[OH:1][C:2]1([C:15]#[C:16][CH2:17][OH:18])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C(O)(=O)C.O>[Pd].C(O)C>[OH:1][C:2]1([CH2:15][CH2:16][CH2:17][OH:18])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 21955143Tert-butyl 4-hydroxy-4-(3-hydroxyprop-1-yn-1-yl)piperidine-1-carboxylate

Product 1

HCID 21955351HCID 21955351, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium on carbon (5%, 800 mg) was added to a solution of 1,1-dimethylethyl 4-hydroxy-4-(3-hydroxypropynyl)-1-piperidinecarboxylate (from step (ii) above; 8.37 g, 32.8 mmol) in ethanol (400 ml), acetic acid (40 ml) and water (5 ml) and the mixture was shaken under an atmosphere of hydrogen (40 psi) for 20 hours. The mixture was filtered through Hyflo™ and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (50:50 increasing to 0:100), to give the title compound (4.84 g, 57%).

Workup

  1. filtrationThe mixture was filtered through Hyflo™
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by flash column chromatography on silica gel
  4. washeluting with isohexane/EtOAc (50:50 increasing to 0:100)

Sources & evidence

ORD record
ord-4c001cacba4e4035812d3bac2396d594
Source dataset
uspto-grants-2008_07
Patent number
US07393858B2

Reaction notes

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