Methyl 1-benzyl-4-(3-hydroxy-1-propin-1-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate → HCID 59398352, compound

HRID 39714Notes

Reaction equation

HRID 39714 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:14]#[C:15][CH2:16][OH:17])=[C:10]([C:18]([O:20][CH3:21])=[O:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[C].[Pd].C(O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][OH:17])[CH:10]([C:18]([O:20][CH3:21])=[O:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 59398219Methyl 1-benzyl-4-(3-hydroxy-1-propin-1-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate

Product 1

HCID 59398352HCID 59398352, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 702EthanolSolvent

Procedure

To 40 mL of an ethanol solution containing 2.6 g of methyl 1-benzyl-4-(3-hydroxy-1-propin-1-yl)-1,2,5,6-tetrahydropyridine-3-carboxylate, 1.0 g of palladium carbon was added, and the mixture was stirred for 2 hours under a hydrogen atmosphere. Thereto was added 0.7 g of palladium carbon, and the mixture was stirred for 2 hours under a hydrogen atmosphere. The insoluble material filtered off, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; hexane:ethyl acetate 1:2] to obtain 0.50 g of a brown oily substance, methyl 1-benzyl-4-(3-hydroxypropyl)piperidine-3-carboxylate.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 2 hours under a hydrogen atmosphere
  3. filtrationThe insoluble material filtered off
  4. customthe solvent was removed under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by silica gel column chromatography [eluent; hexane:ethyl acetate 1:2]

Sources & evidence

ORD record
ord-9181ad71acda4de5a70aeac0174a55c1
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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