HCID 14117018, compound → HCID 69137346, compound

HRID 1871198Notes

Reaction equation

HRID 1871198 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-b7aea3f23437423ba7a2a8e3626de760
Source dataset
uspto-grants-2000_08
Patent number
US06103487

Reaction notes

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