trans-3-Cyclopropylmethoxy-4-azidotetrahydrofuran → trans-3-Cyclopropylmethoxy-4-aminotetrahydrofuran

HRID 398391Notes

Reaction equation

HRID 398391 reaction equation
[CH:1]1([CH2:4][O:5][C@H:6]2[C@H:10]([N:11]=[N+]=[N-])[CH2:9][O:8][CH2:7]2)[CH2:3][CH2:2]1>CCOC(C)=O.[Pd]>[CH:1]1([CH2:4][O:5][C@H:6]2[C@H:10]([NH2:11])[CH2:9][O:8][CH2:7]2)[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 131724050trans-3-Cyclopropylmethoxy-4-azidotetrahydrofuran

Product 1

HCID 70024767trans-3-Cyclopropylmethoxy-4-aminotetrahydrofuran

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of trans-3-cyclopropylmethoxy-4-azidotetrahydrofuran from step 3 above (1.2 g, mmol, 6.55 mmol) and 10% Pd on carbon (150 mg) in EtOAc (35 mL) was stirred under an atmosphere of hydrogen at ambient pressure and ambient temperature for 6 h. The catalyst was removed by filtration and the filtrate solvents were removed in vacuo to give the title compound as an oil (1.1 g, TLC Rf=0.3, 95:5:0.25 CH2Cl2:MeOH:NH4OH).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate solvents were removed in vacuo

Sources & evidence

ORD record
ord-85099aea01ea450ea620184891a84ca8
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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