HCID 86688121, compound → HCID 66800463, compound

HRID 408018Notes

Reaction equation

HRID 408018 reaction equation
[CH3:1][S:2]([C:5]1[N:10]=[CH:9][C:8]([NH:11][C@H:12]2[CH2:16][CH2:15][N:14]([CH:17]3[CH2:22][CH2:21][N:20](C(OCC4C=CC=CC=4)=O)[CH2:19][CH2:18]3)[C:13]2=[O:33])=[CH:7][CH:6]=1)(=[O:4])=[O:3]>CO.[Pd]>[CH3:1][S:2]([C:5]1[N:10]=[CH:9][C:8]([NH:11][C@H:12]2[CH2:16][CH2:15][N:14]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:13]2=[O:33])=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

4

Reactant 1

HCID 86688121HCID 86688121, compound

Product 1

HCID 66800463HCID 66800463, compoundYield 104.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

(S)-Benzyl 4-(3-(6-(methylsulfonyl)pyridin-3-ylamino)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (0.23 g, 0.49 mmol) was dissolved in MeOH (5 mL) and cooled to 0° C. The material was purged with N2 by three vacuum pump/N2 balloon cycles. Palladium on carbon (10 wt. % dry basis, wet, Degussa type, 0.053 g, 0.49 mmol) was added and the system was purged with 1 atm H2 by three vacuum pump/H2 balloon cycles. The reaction continued to stir under H2 until the starting material was consumed. The mixture was filtered through GF/F paper and concentrated to give (S)-3-(6-(methylsulfonyl)pyridin-3-ylamino)-1-(piperidin-4-yl)pyrrolidin-2-one (0.17 g, 0.51 mmol, 100% yield).

Workup

  1. customThe material was purged with N2 by three vacuum pump/N2 balloon cycles
  2. customthe system was purged with 1 atm H2 by three vacuum pump/H2 balloon cycles
  3. customwas consumed
  4. filtrationThe mixture was filtered through GF/F paper
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-19d702d5fb4d40228e0c5e08b4c0b599
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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