6-Oxabicyclo[3.1.0]hexane → HCID 13737690, compound

HRID 2357308Notes

Reaction equation

HRID 2357308 reaction equation
[CH:1]12[O:6][CH:2]1[CH2:3][CH2:4][CH2:5]2.[N-:7]=[N+:8]=[N-:9].[Na+].[NH4+].[Cl-]>CO.O>[N:7]([C@@H:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[OH:6])=[N+:8]=[N-:9]

Participants

6

Reactant 3

HCID 92446-Oxabicyclo[3.1.0]hexaneHCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 13737690HCID 13737690, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a soln of cyclopenteneoxide (2.0 g, 23.8 mmol) in CH3OH and H2O (40 mL) (4/1, v/v), were added NaN3 (7.73 g, 119 mmol) and NH4Cl (3.17 g, 59.2 mmol). The resulting mixture was heated to solvent reflux for 18 h then cooled to 23°. The mixture was concentrated and the residue was diluted with EtOAc, washed with H2O, the organic layer was dried over Na2SO4, concentrated to give the desired product (2.8 g, 93%). 1H NMR (CDCl3): δ4.10 (m, 1H), 3.72 (m, 1H), 2.10 (m, 2H), 1.72-1.60 (m, 4H).

Workup

  1. temperatureThe resulting mixture was heated to solvent
  2. temperaturereflux for 18 h
  3. temperaturethen cooled to 23°
  4. concentrationThe mixture was concentrated
  5. additionthe residue was diluted with EtOAc
  6. washwashed with H2O
  7. dry with materialthe organic layer was dried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c3c3d17b1aa544d6a8b6bbc944b4ca42
Source dataset
uspto-grants-2010_07
Patent number
US07759486B2

Reaction notes

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