Methanol → (2s,3s,5s)-3-(Methoxycarbonyl)-5-[(pyrrolidin-1-ylcarbonyl)oxy]piperidine-2-carboxylic acid

HRID 535071Notes

Reaction equation

HRID 535071 reaction equation
C([N:8]1[CH2:13][C@@H:12]([O:14][C:15]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])[CH2:11][C@H:10]([C:22]([O:24][CH3:25])=[O:23])[C@H:9]1[C:26]([O:28]CC1C=CC=CC=1)=[O:27])C1C=CC=CC=1.CO.[H][H]>[Pd]>[CH3:25][O:24][C:22]([C@H:10]1[CH2:11][C@H:12]([O:14][C:15]([N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)=[O:16])[CH2:13][NH:8][C@@H:9]1[C:26]([OH:28])=[O:27])=[O:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 1317319292-benzyl 3-methyl (2S,3S,5S)-1-benzyl-5-[(pyrrolidin-1-ylcarbonyl)oxy]piperidine-2,3-dicarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 67304698(2s,3s,5s)-3-(Methoxycarbonyl)-5-[(pyrrolidin-1-ylcarbonyl)oxy]piperidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 2-benzyl 3-methyl (2S,3S,5S)-1-benzyl-5-[(pyrrolidin-1-ylcarbonyl)oxy]piperidine-2,3-dicarboxylate (144 mg, 0.000300 mol) in methanol (3.0 mL, 0.074 mol) was hydrogenated in the presence of 10% Pd/C, under balloon pressure of hydrogen, overnight. After filtered off the catalyst, the filtration was concentrated to dry to provide crude product, which was used directly in next step.

Workup

  1. filtrationAfter filtered off the catalyst
  2. filtrationthe filtration
  3. concentrationwas concentrated
  4. customto dry
  5. customto provide crude product, which

Sources & evidence

ORD record
ord-726fdcae8b444aaabe78f90b1b85b5c1
Source dataset
uspto-grants-2014_10
Patent number
US08853243B2

Reaction notes

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