HCID 14117018, compound → HCID 69137346, compound

HRID 1292684Notes

Reaction equation

HRID 1292684 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH2:21][N:22]=[N+]=[N-])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH2:21][NH2:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 14117018HCID 14117018, compound

Product 1

HCID 69137346HCID 69137346, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-t-butoxycarbonyl-4(R)-t-butyldimethylsilyloxy-2(S)-azidomethylpyrrolidine (9.06 g, 25.39 mmol) in EtOAc (120 ml) was purged with argon and 10% palladium on carbon (1.05 g) added. The flask was evacuated and stirred under an atmosphere of hydrogen (49 psi) for 16 hrs. The hydrogen was replaced by argon, the catalyst removed by filtration and the solvent evaporated in vacuo. The residue was chromatographed (SiO2, 2.5 to 5% saturated NH4OH in acetonitrile, gradient elution), to afford the title compound as an oil.

Workup

  1. additionadded
  2. customThe flask was evacuated
  3. customthe catalyst removed by filtration
  4. customthe solvent evaporated in vacuo
  5. customThe residue was chromatographed
  6. wash(SiO2, 2.5 to 5% saturated NH4OH in acetonitrile, gradient elution)

Sources & evidence

ORD record
ord-267129cee8b74e1298b2f6d8e70fe8a6
Source dataset
uspto-grants-1998_05
Patent number
US05756528

Reaction notes

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