HCID 18727259, compound → HCID 18727271, compound

HRID 366494Notes

Reaction equation

HRID 366494 reaction equation
C([O:8][N:9]([CH3:37])[C:10]([C@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][N:13]1[S:18]([N:21]1[CH2:26][CH2:25][CH:24]([C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[C:33]([F:36])[CH:34]=3)[NH:29][CH:28]=2)[CH2:23][CH2:22]1)(=[O:20])=[O:19])=[O:11])C1C=CC=CC=1>C(O)C.O1CCCC1.[Pd]>[OH:8][N:9]([CH3:37])[C:10]([C@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][N:13]1[S:18]([N:21]1[CH2:26][CH2:25][CH:24]([C:27]2[C:35]3[C:30](=[CH:31][CH:32]=[C:33]([F:36])[CH:34]=3)[NH:29][CH:28]=2)[CH2:23][CH2:22]1)(=[O:20])=[O:19])=[O:11]

Participants

4

Reactant 1

HCID 18727259HCID 18727259, compound

Product 1

HCID 18727271HCID 18727271, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A suspension of 10% Pd/C (0.20 g) and N-benzyloxy-N-methyl-1-[4-(5-fluoroindol-3-yl)piperidine-1-sulfonyl]piperidine-2-(R)-carboxamide (0.40 g, 0.75 mmol) [prepared as described in Step 4 above] in 80% ethanol/tetrahydrofuran (6 ml) was stirred under a hydrogen atmosphere (1 atm) for 70 min. The reaction was degassed with nitrogen, filtered through Celite and the filtrate was concentrated in vacuo. The residue was chromatographed (PTLC, SiO2, 10% methanol/methylene chloride) to give N-hydroxy-N-methyl-1-[4-(5-fluoroindol-3-yl)piperidine-1-sulfonyl]piperidine-2-(R)-carboxamide (83%) as a white solid.

Workup

  1. customThe reaction was degassed with nitrogen
  2. filtrationfiltered through Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was chromatographed (PTLC, SiO2, 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-81818eae506d41f6a8b2ef15aeb2ef6d
Source dataset
uspto-grants-2000_10
Patent number
US06130220

Reaction notes

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