HCID 58386810, compound → HCID 58386808, compound

HRID 73555Notes

Reaction equation

HRID 73555 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][C@@H:13]2[O:16][C:17](=[O:26])[N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@@H:12]2[CH2:11]1)([O-])=O>CCO.CCOC(C)=O.[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][C@@H:13]2[O:16][C:17](=[O:26])[N:18]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[C@@H:12]2[CH2:11]1

Participants

5

Reactant 1

HCID 58386810HCID 58386810, compound

Product 1

HCID 58386808HCID 58386808, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3aR,7aS)-tert-butyl 5-(3-nitropyridin-4-yl)-2-oxohexahydrooxazolo[4,5-c]pyridine-3(2H)-carboxylate in EtOH and EtOAc (1:1, 0.15 M) was added Pd/C (10% by weight) and the reaction was stirred under a hydrogen balloon for 15 h. The solution was filtered through a pad of Celite, and the filtrate was concentrated to yield (3aR,7aS)-tert-butyl 5-(3-aminopyridin-4-yl)-2-oxohexahydrooxazolo[4,5-c]pyridine-3(2H)-carboxylate as a clear oil in >95% yield. LCMS (m/z): 335.0 (MH+), Rt=1.68 min.

Workup

  1. filtrationThe solution was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b14e3ee28439484cae27e2159f239950
Source dataset
uspto-grants-2014_09
Patent number
US08829193B2

Reaction notes

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