3-Azido-6-methoxyhexahydrofuro[3,2-b]furan → 6-Methoxyhexahydrofuro[3,2-b]furan-3-amine

HRID 1053934Notes

Reaction equation

HRID 1053934 reaction equation
[N:1]([CH:4]1[CH2:8][O:7][CH:6]2[CH:9]([O:12][CH3:13])[CH2:10][O:11][CH:5]12)=[N+]=[N-]>CO.[Pd]>[CH3:13][O:12][CH:9]1[CH:6]2[O:7][CH2:8][CH:4]([NH2:1])[CH:5]2[O:11][CH2:10]1

Participants

4

Reactant 1

HCID 1183879903-Azido-6-methoxyhexahydrofuro[3,2-b]furan

Product 1

HCID 756144396-Methoxyhexahydrofuro[3,2-b]furan-3-amineYield 52.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-azido-6-methoxyhexahydrofuro[3,2-b]furan (0.85 g, 4.6 mmol) in MeOH (50 mL) was added Pd/C (10%, 94.5 mg). The reaction was stirred at rt overnight in 1 atm H2 atmosphere, then the mixture was filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (0.02 M NH3) (v/v)=25/1) to give the title compound as colorless oil (380 mg, 52.1%).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (DCM/MeOH (0.02 M NH3) (v/v)=25/1)

Sources & evidence

ORD record
ord-5c2dd30b2dd74d3c92405a599e24b4c3
Source dataset
uspto-grants-2016_07
Patent number
US09394281B2

Reaction notes

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