Ammonia → HCID 59169156, compound

HRID 2364677Notes

Reaction equation

HRID 2364677 reaction equation
[N:1]([C@@H:4]1[CH2:10][CH:9]2[C@@H:7]([O:8]2)[CH2:6][C@H:5]1[OH:11])=[N+:2]=[N-:3].[NH3:12]>C(O)C>[NH2:12][C@@H:7]1[CH2:6][C@@H:5]([OH:11])[C@H:4]([N:1]=[N+:2]=[N-:3])[CH2:10][C@H:9]1[OH:8]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86668244HCID 86668244, compound

Product 1

HCID 59169156HCID 59169156, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(1S,3R,4R)-4-Azido-7-oxabicyclo[4.1.0]heptan-3-ol 3d (600 mg, 3.87 mmol) was dissolved in 20 mL ethanol followed by the addition of 10 mL of aqueous ammonia. The resulting solution was heated to reflux for 4 hours, then cooled down to room temperature and stirred for another 12 hours. The reaction solution was concentrated under reduced pressure to obtain the crude title compound (1R,2R,4R,5R)-2-amino-5-azido-cyclohexane-1,4-diol 3e (665 mg, as a yellow oil), which was used in the next step without further furification.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 4 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-54b2a384b35546f08eda77ff64cec00b
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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