HCID 67130624, compound → HCID 67130707, compound

HRID 1920234Notes

Reaction equation

HRID 1920234 reaction equation
[CH3:1][C@H:2]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-])=O)[CH2:5][C@H:4]2[N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:18](=[O:20])[O:19][C@H:3]12>CO.[Pd]>[NH2:14][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:8]=1[N:6]1[CH2:7][C@H:2]([CH3:1])[C@H:3]2[O:19][C:18](=[O:20])[N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@@H:4]2[CH2:5]1

Participants

4

Reactant 1

HCID 67130624HCID 67130624, compound

Product 1

HCID 67130707HCID 67130707, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (3aR,7S,7aR)-tert-butyl 7-methyl-5-(3-nitropyridin-4-yl)-2-oxohexahydrooxazolo[4,5-c]pyridine-3(2H)-carboxylate (1.0 equiv.) in methanol, at a concentration of 0.1 M, was added 10% palladium on carbon (0.1 eq.). The resultant heterogeneous solution was put under an atmosphere of hydrogen and was stirred for 14 hours. At this time the mixture was filtered through a pad of celite eluting with methanol. The volatiles were removed in vacuo yielding (3aR,7S,7aR)-tert-butyl 5-(3-aminopyridin-4-yl)-7-methyl-2-oxohexahydrooxazolo[4,5-c]pyridine-3(2H)-carboxylate. LCMS (m/z): 349.1 (MH+); LC Rt=2.18 min.

Workup

  1. filtrationAt this time the mixture was filtered through a pad of celite
  2. washeluting with methanol
  3. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-27283c92b49e4df7b7d926877e2c61fe
Source dataset
uspto-grants-2012_05
Patent number
US08168794B2

Reaction notes

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