Ammonium formate → 2-Boc-2,6-diazaspiro(3.3)heptane

HRID 1929572Notes

Reaction equation

HRID 1929572 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]2([CH2:14][N:13](C(C3C=CC=CC=3)C)[CH2:12]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>[Pd].CO>[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]2([CH2:12][NH:13][CH2:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59326771HCID 59326771, compound

Product 1

HCID 401519812-Boc-2,6-diazaspiro(3.3)heptaneYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A flask containing 6-(1-phenyl-ethyl)-2,6-diaza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester (200 mg, 0.66 mmol), ammonium formate (4.22 g, 67 mmol), 10% palladium on carbon (40 mg) and methanol (10 mL) was evacuated and filled with argon. The resulting mixture was stirred at 65° C. for 3 hours, then filtered and concentrated in vacuo to afford 2,6-diaza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester (130 mg, 99%) as a brown viscous oil which was used for the next step without further purification.

Workup

  1. customwas evacuated
  2. additionfilled with argon
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c8d20e7257443d6a04b4d3236fe2f51
Source dataset
uspto-grants-2012_05
Patent number
US08188090B2

Reaction notes

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