1,1-Dimethylethyl 4-(3-ethoxy-3-oxo-1-propyn-1-yl)-4-hydroxy-1-piperidinecarboxylate → tert-Butyl 4-(3-ethoxy-3-oxopropyl)-4-hydroxypiperidine-1-carboxylate

HRID 747009Notes

Reaction equation

HRID 747009 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]#[C:6][C:7]1([OH:20])[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)[CH3:2]>[Pd].O.C(O)C>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH2:6][C:7]1([OH:20])[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:11][CH2:12]1)[CH3:2]

Participants

5

Reactant 1

HCID 219552401,1-Dimethylethyl 4-(3-ethoxy-3-oxo-1-propyn-1-yl)-4-hydroxy-1-piperidinecarboxylate

Product 1

HCID 21955349tert-Butyl 4-(3-ethoxy-3-oxopropyl)-4-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Palladium on carbon (5%, 1 g) in water (10 ml) was added to a solution of 1,1-dimethylethyl 4-(3-ethoxy-3-oxo-1-propynyl)-4-hydroxy-1-piperidinecarboxylate (from step (i) above; 14.6 g, 0.046 mol) in ethanol (200 ml) and the mixture was shaken under hydrogen (45 psi) for 90 minutes. The mixture was filtered through a glass fibre pad and the solvent was evaporated under reduced pressure to give the title compound.

Workup

  1. filtrationThe mixture was filtered through a glass fibre pad
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-184bf1368d2f4a8bbabe92e725b325ed
Source dataset
uspto-grants-2008_07
Patent number
US07393858B2

Reaction notes

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