1-Piperidinecarboxylic acid, 3-fluoro-4-methoxy-4-[(phenylmethoxy)methyl]-, 1,1-dimethylethyl ester, (3R,4S)-rel- → HCID 71268706, compound

HRID 70790Notes

Reaction equation

HRID 70790 reaction equation
C([O:8][CH2:9][C@@:10]1([O:24][CH3:25])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][C@H:11]1[F:23])C1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].CO>[F:23][C@H:11]1[C@:10]([CH2:9][OH:8])([O:24][CH3:25])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]1

Participants

5

Reactant 2

HCID 712687041-Piperidinecarboxylic acid, 3-fluoro-4-methoxy-4-[(phenylmethoxy)methyl]-, 1,1-dimethylethyl ester, (3R,4S)-rel-HCID 178418361HCID 178418361, compound

Product 1

HCID 71268706HCID 71268706, compoundYield 110.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

20% palladium hydroxide on carbon powder (102 mg) was suspended in a MeOH (29 ml) solution of tert-butyl rel-(3R,4S)-4-[(benzyloxy)methyl]-3-fluoro-4-methoxypiperidine-1-carboxylate (971 mg), and stirring was performed at room temperature under a flow of hydrogen gas for 4 hours. After filtration through Celite, the filtrate was concentrated to obtain tert-butyl rel-(3R,4S)-3-fluoro-4-(hydroxymethyl)-4-methoxypiperidine-1-carboxylate (800 mg).

Workup

  1. filtrationAfter filtration through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-37b11161ef7a43c489c5dec85941b950
Source dataset
uspto-grants-2014_09
Patent number
US08822688B2

Reaction notes

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