Hydrochloric Acid → 6-(Methylamino)hexahydrofuro[3,2-b]furan-3-ol

HRID 1053912Notes

Reaction equation

HRID 1053912 reaction equation
[CH2:1]([N:8](C)[CH:9]1[CH2:13][O:12][CH:11]2[CH:14]([O:17]CC3C=CC=CC=3)[CH2:15][O:16][CH:10]12)C1C=CC=CC=1.Cl>CCO.[Pd]>[CH3:1][NH:8][CH:9]1[CH:10]2[O:16][CH2:15][CH:14]([OH:17])[CH:11]2[O:12][CH2:13]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118387971N-benzyl-6-(benzyloxy)-N-methylhexahydrofuro[3,2-b]furan-3-amine

Product 1

HCID 129593416-(Methylamino)hexahydrofuro[3,2-b]furan-3-olYield 88.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-benzyl-6-(benzyloxy)-N-methylhexahydrofuro[3,2-b]furan-3-amine (5.10 g, 15 mmol) in EtOH (40 mL) were added Pd/C (10% wt, 1.0 g) and concentrated HCl (36.5%, 2 mL) in a autoclave under 5 MPa H2. The reaction mixture was stirred at 60° C. overnight and filtered. The filtrate was concentrated in vacuo to give the title compound as yellow oil (2.12 g, 88.6%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-31b9b191d02947e39e3ee3db607d904d
Source dataset
uspto-grants-2016_07
Patent number
US09394281B2

Reaction notes

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