HCID 54549910, compound → tert-butyl N-{6-azaspiro[3.4]octan-8-yl}carbamate

HRID 1445274Notes

Reaction equation

HRID 1445274 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[C:13]2([CH2:16][CH2:15][CH2:14]2)[CH2:12][N:11]([C@@H](C2C=CC=CC=2)C)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][CH:9]1[C:13]2([CH2:14][CH2:15][CH2:16]2)[CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 54549910HCID 54549910, compound

Product 1

HCID 19354273tert-butyl N-{6-azaspiro[3.4]octan-8-yl}carbamateYield 102.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4.1 g of 8-tert-butoxycarbonylamino-6-[1-(R)-phenylethyl]-6-azaspiro[3.4]octane in 60 ml of ethanol there was added 4.5 g of 5% palladium on charcoal (50% wet) and reduction was carried out under a hydrogen atmosphere (H2 pressure: 4 atm.) for 5 hrs. During the reduction, the reaction vessel was warmed by irradiation with a tungsten lamp. At 1 hr. from the beginning of the reduction, 2 g of the same catalyst was further added and the reduction continued for an additional 4 hours at the same condition to total 5 hours. The catalyst was removed by filtration and the solvent was removed under reduced pressure to yield 2.88 g of the titled compound.

Workup

  1. customfor 5 hrs
  2. temperatureDuring the reduction, the reaction vessel was warmed by irradiation with a tungsten lamp
  3. waitthe reduction continued for an additional 4 hours at the same condition to total 5 hours
  4. customThe catalyst was removed by filtration
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4aa35c46623640e281d35494f27fb570
Source dataset
uspto-grants-2010_02
Patent number
USRE041149E1

Reaction notes

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