Diethyl Ether → HCID 13186896, compound

HRID 1046520Notes

Reaction equation

HRID 1046520 reaction equation
[CH3:1][C:2]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:3]=1[O:4][C@@H:5]1[CH2:10][CH2:9][N:8](C(OCC2C=CC=CC=2)=O)[CH2:7][C@H:6]1[OH:21].[H][H].C(OCC)C>CO.[Pd]>[CH3:1][C:2]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:3]=1[O:4][C@@H:5]1[CH2:10][CH2:9][NH:8][CH2:7][C@H:6]1[OH:21]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 68894799HCID 68894799, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13186896HCID 13186896, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of trans-benzyl 4-(2,3-dimethylphenoxy)-3-hydroxypiperidine-1-carboxylate (3.5 g, 9.8 mmol) in methanol (50 ml) was added to 5% palladium on charcoal (350 mg) under an atmosphere of nitrogen. The vessel was placed under an atmosphere of hydrogen and stirred vigorously until hydrogen uptake ceased. The resulting suspension was filtered over a short pad of celite (pre-washed with methanol) and the pad washed with a further portion of methanol (100 ml). Concentration of the methanolic solution in vacuo gave a yellow oil. Dilution with diethyl ether (100 ml) yielded trans-4-(2,3-dimethylphenoxy)-3-hydroxypiperidine as a white solid (1.01 g, 50%).

Workup

  1. filtrationThe resulting suspension was filtered over a short pad of celite (pre-washed with methanol)
  2. washthe pad washed with a further portion of methanol (100 ml)
  3. customConcentration of the methanolic solution in vacuo gave a yellow oil

Sources & evidence

ORD record
ord-819a13286c684513a4ac1044a8925c13
Source dataset
uspto-grants-2013_10
Patent number
US08569342B2

Reaction notes

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