HCID 59428662, compound → HCID 16773932, compound

HRID 504148Notes

Reaction equation

HRID 504148 reaction equation
C([O:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][N:12]1[S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)(=[O:19])=[O:18])=[O:10])C1C=CC=CC=1>[Pd].C(O)C>[F:26][C:22]1[CH:21]=[C:20]([S:17]([N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH:11]2[C:9]([OH:10])=[O:8])(=[O:18])=[O:19])[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 1

HCID 59428662HCID 59428662, compound

Product 1

HCID 16773932HCID 16773932, compoundYield 82.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (S)-1-(3-fluoro-benzenesulfonyl)-piperidine-2-carboxylic acid benzyl ester (6.51 g, 17.3 mmol), ethanol (200 mL) and 10% Pd on carbon (1.83 g, 1.70 mmol) was hydrogenated at 30 psi for 3 h. The suspension was then filtered through celite and washed with ethyl acetate. The filtrate was concentrated under reduced pressure. The resulting oil was chromatographed on silica gel (dichloromethane/n-heptane, 9/1) to afford 4.10 g (82.9%) of the title compound.

Workup

  1. filtrationThe suspension was then filtered through celite
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe resulting oil was chromatographed on silica gel (dichloromethane/n-heptane, 9/1)

Sources & evidence

ORD record
ord-19b9b8eda8874fbfb10059216812710e
Source dataset
uspto-grants-2010_08
Patent number
US07777042B2

Reaction notes

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