tert-butyl (2R)-2-(azidomethyl)pyrrolidine-1-carboxylate → Ammonia

HRID 567823Notes

Reaction equation

HRID 567823 reaction equation
[N:1]([CH2:4][C@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[N+]=[N-]>[Pd].C(O)C>[NH3:1].[NH2:1][CH2:4][C@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

5

Reactant 1

HCID 13008760tert-butyl (2R)-2-(azidomethyl)pyrrolidine-1-carboxylate

Product 2

HCID 222AmmoniaHCID 1512534tert-butyl (2R)-2-(aminomethyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on charcoal (750 mg) was added to a solution of tert-butyl (2R)-2-(azidomethyl)-1-pyrrolidinecarboxylate (preperation 51)(5.74 g, 25.39 mmol) in ethanol (100 ml). The reaction mixture was hydrogenated @15 psi for 2.5 hrs, after which time the catalyst was filtered off and the solvent evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (90:10:0.5) as the eluant, to afford the title compound and some starting material. The mixture was dissolved in ethanol (100 ml) and 10% palladium on charcoal (500 mg) was added, the mixture was hydrogenated at 30 psi for 18 hrs, after which time the catalyst was filtered off and the solvent evaporated under reduced pressure to afford the title compound as a clear oil, 4.32 g, (85%).

Workup

  1. customfor 2.5 hrs
  2. filtrationafter which time the catalyst was filtered off
  3. customthe solvent evaporated under reduced pressure
  4. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ce99e8d979f744f7833d64da1ac98e6f
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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