HCID 71268626, compound → tert-Butyl 4-(hydroxymethyl)-4-methoxypiperidine-1-carboxylate

HRID 70781Notes

Reaction equation

HRID 70781 reaction equation
C([O:8][CH2:9][C:10]1([O:23][CH3:24])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)C1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].CO>[OH:8][CH2:9][C:10]1([O:23][CH3:24])[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:14][CH2:15]1

Participants

5

Reactant 2

HCID 71268626HCID 71268626, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23447302tert-Butyl 4-(hydroxymethyl)-4-methoxypiperidine-1-carboxylateYield 78.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

20% palladium hydroxide on carbon (270 mg) was suspended in a MeOH (81 ml) solution of tert-butyl 4-[(benzyloxy)methyl]-4-methoxypiperidine-1-carboxylate (2.7 g), and stirred under a flow of hydrogen gas at room temperature for 4 hours. After filtering using Celite, the filtrate was concentrated, and the residue was purified by silica gel column chromatography (EtOAc) to obtain tert-butyl 4-(hydroxymethyl)-4-methoxypiperidine-1-carboxylate (1.55 g).

Workup

  1. filtrationAfter filtering
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by silica gel column chromatography (EtOAc)

Sources & evidence

ORD record
ord-b2e7828446454020b588376257766377
Source dataset
uspto-grants-2014_09
Patent number
US08822688B2

Reaction notes

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