Ammonium formate → tert-Butyl 6-azaspiro[2.5]octan-1-ylcarbamate

HRID 1654522Notes

Reaction equation

HRID 1654522 reaction equation
C(OC([N:11]1[CH2:26][CH2:25][C:14]2([CH:16]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15]2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[C:21]([O:20][C:18]([NH:17][CH:16]1[C:14]2([CH2:13][CH2:12][NH:11][CH2:26][CH2:25]2)[CH2:15]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 70347143Benzyl 1-{[(tert-butoxy)carbonyl]amino}-6-azaspiro[2.5]octane-6-carboxylate

Product 1

HCID 15282171tert-Butyl 6-azaspiro[2.5]octan-1-ylcarbamateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the title compound of step 5 (2.2 g, 6.10 mmol) in ethanol (60 ml) was added ammonium formate (1.15 g, 18.3 mmol) followed by palladium on activated carbon (10% palladium content, 1.94 g, 1.83 mmol). The mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered, and the filtrate was concentrated in vacuo to afford the title compound as a white foam (1.4 g, 6.1 mmol, yield 100%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-694bdfe2edc745578daaf95a74bc4271
Source dataset
uspto-grants-1995_04
Patent number
US05407943

Reaction notes

Loading…