Ammonium formate → HCID 22609470, compound

HRID 2306787Notes

Reaction equation

HRID 2306787 reaction equation
C([N:8]1[CH2:16][CH:15]2[CH:10]([N:11]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:12][CH2:13][N:14]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[C:20]([O:19][C:17]([N:14]1[CH2:13][CH2:12][N:11]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:10]2[CH:15]1[CH2:16][NH:8][CH2:9]2)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22609551HCID 22609551, compound

Product 1

HCID 22609470HCID 22609470, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 39 mg (0.093 mmol) of 8-benzyl-2,5-bis-tert-butoxycarbonyl-2,5,8-triazabicyclo-[4,3,0]nonane synthesized by the above process in methanol (1.5 ml) were added 40 mg (0.63 mmol) of ammonium formate and 40 mg of 10% palladium on carbon. The mixture was stirred for 1 hour at 70° C. under nitrogen, and the catalyst was removed from the reaction mixture by suction filtration through Celite. The filtrate was concentrated under reduced pressure, and the resultant crude oil was purified by column chromatography on silica gel, thereby obtaining 29 mg (yield: 95%) of 2,5-bis-tert-butoxycarbonyl-2,5,8-triazabicyclo[4,3,0]nonane as a colorless oil.

Workup

  1. customthe catalyst was removed from the reaction mixture by suction filtration through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe resultant crude oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8a0fbcaed3c2449284be81337093be3f
Source dataset
uspto-grants-2004_12
Patent number
US06828316B2

Reaction notes

Loading…