HCID 18727259, compound → HCID 18727271, compound

HRID 843014Notes

Reaction equation

HRID 843014 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 is 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
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was chromatographed (PTLC, SiO2, 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-09b16af3ec0d4ed8a17a029499a1972c
Source dataset
uspto-grants-2002_04
Patent number
US06376506B1

Reaction notes

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