Tert-butyl 3-azidoazetidine-1-carboxylate → Tert-butyl 3-aminoazetidine-1-carboxylate

HRID 1371774Notes

Reaction equation

HRID 1371774 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([N:12]=[N+]=[N-])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([NH2:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 22242836Tert-butyl 3-azidoazetidine-1-carboxylate

Product 1

HCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of the azide (1.15 g, 5.80 mmol, Example 317) in ethanol (20 mL), 10% palladium on carbon (93 mg) was added and the mixture was hydrogenated for 1 hour at 48 psi. The mixture was filtered through a pad of celite and the solvent was removed to a colorless oil. 940 mg, 94%. The compound was directly used for the next step.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. customthe solvent was removed to a colorless oil

Sources & evidence

ORD record
ord-42148a595a24469fb9e5da47401efe97
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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