Hydrochloric Acid → 6-Aminohexahydrofuro[3,2-b]furan-3-ol hydrochloride

HRID 1053919Notes

Reaction equation

HRID 1053919 reaction equation
O1CCCCC1[O:7][CH:8]1[CH:12]2[O:13][CH2:14][CH:15]([NH2:16])[CH:11]2[O:10][CH2:9]1.[ClH:17]>C(Cl)Cl.CCOC(C)=O>[ClH:17].[NH2:16][CH:15]1[CH:11]2[O:10][CH2:9][CH:8]([OH:7])[CH:12]2[O:13][CH2:14]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 1183879826-((tetrahydro-2H-pyran-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-amine

Product 1

HCID 1183879596-Aminohexahydrofuro[3,2-b]furan-3-ol hydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-((tetrahydro-2H-pyran-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-amine (2.8 g, 12.2 mmol) in DCM (50 mL) was added a solution of HCl in EtOAc (15 mL, 3.8M), and the mixture was stirred at rt overnight and concentrated in vacuo. The residue was washed with DCM (50 mL), and then dried in vacuo at 60° C. overnight to give the crude product as a brown solid (3.3 g, not pure).

Workup

  1. concentrationconcentrated in vacuo
  2. washThe residue was washed with DCM (50 mL)
  3. customdried in vacuo at 60° C. overnight

Sources & evidence

ORD record
ord-989bc7cfa490497fb966ad708d4ea05f
Source dataset
uspto-grants-2016_07
Patent number
US09394281B2

Reaction notes

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