(3R,5R)-3-(tert-butyldimethylsilyloxy)-5-fluoro-1-(4-methoxybenzyl)piperidine → (3R,5R)-3-(tert-butyldimethylsilyloxy)-5-fluoropiperidine

HRID 73539Notes

Reaction equation

HRID 73539 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:14][C@@H:13]([F:15])[CH2:12][N:11](CC2C=CC(OC)=CC=2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CO.[Pd]>[Si:1]([O:8][C@@H:9]1[CH2:14][C@@H:13]([F:15])[CH2:12][NH:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 59455774(3R,5R)-3-(tert-butyldimethylsilyloxy)-5-fluoro-1-(4-methoxybenzyl)piperidine

Product 1

HCID 59455637(3R,5R)-3-(tert-butyldimethylsilyloxy)-5-fluoropiperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (3R,5R)-3-(tert-butyldimethylsilyloxy)-5-fluoro-1-(4-methoxybenzyl)piperidine (1 eq) in 5 mL of methanol was added 10% Pd/C (0.2 eq). The resulting suspension was stirred at H2 atmosphere overnight. The crude solids were filtered through a pad of Celite on a paper lined Buchner funnel, washed with MeOH, then concentrated in vacuo to yield (3R,5R)-3-(tert-butyldimethylsilyloxy)-5-fluoropiperidine, which was used to next step without further purification. LC/MS (m/z): 234.1 (MH+).

Workup

  1. filtrationThe crude solids were filtered through a pad of Celite on a paper
  2. washwashed with MeOH
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-883f84cca2fd4725b83cfee90578f6e4
Source dataset
uspto-grants-2014_09
Patent number
US08829193B2

Reaction notes

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