HCID 68153568, compound → HCID 68153523, compound

HRID 1405369Notes

Reaction equation

HRID 1405369 reaction equation
[CH3:1][N:2]1[C:14]2([CH2:19][CH2:18][N:17](C(OCC3C=CC=CC=3)=O)[CH2:16][CH2:15]2)[C:6]2=[CH:7][CH:8]=[C:9]([S:10]([CH3:13])(=[O:12])=[O:11])[N:5]2[CH2:4][CH2:3]1>CCO.[C].[Pd]>[CH3:1][N:2]1[C:14]2([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[C:6]2=[CH:7][CH:8]=[C:9]([S:10]([CH3:13])(=[O:11])=[O:12])[N:5]2[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 68153568HCID 68153568, compound

Product 1

HCID 68153523HCID 68153523, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of benzyl 2-methyl-6-methylsulfonyl-spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4′-piperidine]-1′-carboxylate (520 mg, 1.25 mmol) in EtOH (13 mL) was added 10% palladium-carbon (66 mg, 0.062 mmol) under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 16 h under a hydrogen atmosphere. The mixture was filtered through a plug of celite and the solvent was evaporated under reduced pressure to yield 2-methyl-6-methylsulfonyl-spiro[3,4-dihydropyrrolo[1,2-a]pyrazine-1,4′-piperidine] (342 mg, 97%) as an off-white solid. ESI-MS m/z calc. 283.1, found 284.3 (M+1)+; Retention time: 0.30 minutes (3 min run).

Workup

  1. filtrationThe mixture was filtered through a plug of celite
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-87c0bfd206684743993ee33a066d3fb6
Source dataset
uspto-grants-2014_12
Patent number
US08916565B2

Reaction notes

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