HCID 86635350, compound → HCID 68995056, compound

HRID 657085Notes

Reaction equation

HRID 657085 reaction equation
[OH:1][C@@H:2]1[CH2:6][N:5]([CH2:7][CH2:8][N:9]2[C:14](=[O:15])[CH:13]=[N:12][C:11]3[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[N:19][C:10]2=3)[CH2:4][C@@H:3]1[CH2:22][NH:23]C(=O)OCC1C=CC=CC=1>CO.[Pd].[O-2].[Mn+4].[O-2]>[NH2:23][CH2:22][C@@H:3]1[C@H:2]([OH:1])[CH2:6][N:5]([CH2:7][CH2:8][N:9]2[C:14](=[O:15])[CH:13]=[N:12][C:11]3[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[N:19][C:10]2=3)[CH2:4]1

Participants

5

Reactant 1

HCID 86635350HCID 86635350, compound

Product 1

HCID 68995056HCID 68995056, compoundYield 85.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolvent2×

Procedure

A solution of phenylmethyl [((3S,4S)-4-hydroxy-1-{2-[6-(methyloxy)-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate (1.0 g, 2.2 mmol) in methanol was treated with 10% Pd/C (0.44 g) and shaken under 15 psi at room temperature for 2 hours. Pd was filtered through Celite®, the filtrate was concentrated. The residue was redissolved in DCM (20 mL) and methanol (5 mL), treated with manganese(IV) oxide (561 mg, 6.6 mmol), and stirred at room temperature for 2 hours. Solid was filtered and filtrate was concentrated to give product (0.6 g, 85%).

Workup

  1. filtrationPd was filtered through Celite®
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was redissolved in DCM (20 mL)
  4. stirringstirred at room temperature for 2 hours
  5. filtrationSolid was filtered
  6. concentrationfiltrate was concentrated

Sources & evidence

ORD record
ord-db5fe4417f6d443584a17ceb2e253f2e
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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