HCID 67037408, compound → 1-(1,1-Dimethylethyl) 4-ethyl 4-(hydroxymethyl)-1,4-piperidinedicarboxylate

HRID 1777347Notes

Reaction equation

HRID 1777347 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:19][O:20]CC2C=CC=CC=2)[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1([CH2:19][OH:20])[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 67037408HCID 67037408, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 542288591-(1,1-Dimethylethyl) 4-ethyl 4-(hydroxymethyl)-1,4-piperidinedicarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5% Pd/C (1.85 g, 50% wet) is added to a solution of 4-benzyloxymethylpiperidine-1,4-dicarboxylic acid-1-tert-butyl ester-4-ethyl ester (1.85 g, 0.0049 mol) in ethanol (20 mL). The reaction mixture is stirred under the positive pressure of hydrogen gas for 16 hrs at room temperature. The reaction mixture is filtered through celite bed and washed with a solution methanol and dichloromethane (1:5, 100 mL). Combine filtrate is concentrated under reduced pressure to give 4-hydroxymethylpiperidine-1,4-dicarboxylic acid 1-tert-butyl ester-4-ethyl ester.

Workup

  1. filtrationThe reaction mixture is filtered through celite bed
  2. washwashed with a solution methanol and dichloromethane (1:5, 100 mL)
  3. concentrationCombine filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-69d201d497fe47b89cb69258ac8216d2
Source dataset
uspto-grants-2016_02
Patent number
US09266867B2

Reaction notes

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