(3S,5S,6S)-5-[(hydroxyamino)carbonyl]-1-methyl-6-[(4-phenyl-3,6-dihydropyridin-1(2H)-yl)carbonyl]piperidin-3-yl pyrrolidine-1-carboxylate → (3S,5S,6S)-5-[(hydroxyamino)carbonyl]-1-methyl-6-[(4-phenylpiperidin-1-yl)carbonyl]piperidin-3-yl pyrrolidine-1-carboxylate

HRID 61458Notes

Reaction equation

HRID 61458 reaction equation
[N:1]1([C:6]([O:8][C@H:9]2[CH2:14][C@H:13]([C:15]([NH:17][OH:18])=[O:16])[C@@H:12]([C:19]([N:21]3[CH2:26][CH:25]=[C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:23][CH2:22]3)=[O:20])[N:11]([CH3:33])[CH2:10]2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[N:1]1([C:6]([O:8][C@H:9]2[CH2:14][C@H:13]([C:15]([NH:17][OH:18])=[O:16])[C@@H:12]([C:19]([N:21]3[CH2:26][CH2:25][CH:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:23][CH2:22]3)=[O:20])[N:11]([CH3:33])[CH2:10]2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 86598251(3S,5S,6S)-5-[(hydroxyamino)carbonyl]-1-methyl-6-[(4-phenyl-3,6-dihydropyridin-1(2H)-yl)carbonyl]piperidin-3-yl pyrrolidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 86598250(3S,5S,6S)-5-[(hydroxyamino)carbonyl]-1-methyl-6-[(4-phenylpiperidin-1-yl)carbonyl]piperidin-3-yl pyrrolidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 887MethanolSolvent

Procedure

A solution of (3S,5S,6S)-5-[(hydroxyamino)carbonyl]-1-methyl-6-[(4-phenyl-3,6-dihydropyridin-1(2H)-yl)carbonyl]piperidin-3-yl pyrrolidine-1-carboxylate (5.0 mg, 0.000011 mol) TFA salt in 1 mL of MeOH was hydrogenated in the presence of 5% Pd/BaSO4, under a balloon pressure of hydrogen, for 2 h. After filtered off the catalyst, the filtration was concentrated to dry to give the product (5.0 mg, 100%). MS (ESI): (M+H)+=459.15.

Workup

  1. filtrationAfter filtered off the catalyst
  2. filtrationthe filtration
  3. concentrationwas concentrated
  4. customto dry

Sources & evidence

ORD record
ord-68fccff24262489a9e2b463e97495487
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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