1,4-Dioxane hydrochloride → (3SR,4RS)-4-hydrazinyltetrahydrofuran-3-ol hydrochloride

HRID 1043885Notes

Reaction equation

HRID 1043885 reaction equation
O1CCOCC1.[ClH:7].[OH:8][CH:9]1[CH2:13][O:12][CH2:11][CH:10]1[NH:14][NH:15]C(OC(C)(C)C)=O>CO>[ClH:7].[NH:14]([CH:10]1[CH2:11][O:12][CH2:13][CH:9]1[OH:8])[NH2:15]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86686323t-butyl 2-((3RS,4SR)-4-hydroxytetrahydrofuran-3-yl)hydrazinecarboxylate

Product 1

HCID 86686324(3SR,4RS)-4-hydrazinyltetrahydrofuran-3-ol hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4 M hydrogen chloride-1,4-dioxane solution (50 mL) was added to a solution of t-butyl 2-((3RS,4SR)-4-hydroxytetrahydrofuran-3-yl)hydrazinecarboxylate (5.78 g) in methanol (30 mL) under ice-cooling, and the mixture was then warmed to room temperature and stirred overnight. The reaction mixture was concentrated to give the title compound (5 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-2a0fc353c9dd48bfa2d7ccc7df69d076
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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