3-Azido-6-(2-(benzyloxy)ethoxy)hexahydrofuro[3,2-b]furan → 2-((6-Aminohexahydrofuro[3,2-b]furan-3-yl)oxy)ethanol

HRID 1053926Notes

Reaction equation

HRID 1053926 reaction equation
[N:1]([CH:4]1[CH2:8][O:7][CH:6]2[CH:9]([O:12][CH2:13][CH2:14][O:15]CC3C=CC=CC=3)[CH2:10][O:11][CH:5]12)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH:4]1[CH:5]2[O:11][CH2:10][CH:9]([O:12][CH2:13][CH2:14][OH:15])[CH:6]2[O:7][CH2:8]1

Participants

4

Reactant 1

HCID 1183879963-Azido-6-(2-(benzyloxy)ethoxy)hexahydrofuro[3,2-b]furan

Product 1

HCID 1183879542-((6-Aminohexahydrofuro[3,2-b]furan-3-yl)oxy)ethanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 3-azido-6-(2-(benzyloxy)ethoxy)hexahydrofuro[3,2-b]furan (crude product) in MeOH (20 mL) was added Pd/C (10%, 0.31 g). The mixture was stirred at room temperature under a H2 atmosphere overnight. The mixture was filtered and washed with MeOH (20 mL). The filtrate was concentrated in vacuo to give the crude product as brown liquid. The residue was used in the next reaction without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with MeOH (20 mL)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cf87f55273084ec5bc87d31150ee34b3
Source dataset
uspto-grants-2016_07
Patent number
US09394281B2

Reaction notes

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