HCID 20467711, compound → HCID 54399885, compound

HRID 1903008Notes

Reaction equation

HRID 1903008 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][N:8]1[C:11](=[O:12])[CH2:10][CH:9]1[C:13](OCC)=[O:14])=[O:5])[CH3:2]>C(O)C>[CH2:1]([O:3][C:4]([CH2:6][CH2:7][N:8]1[CH:9]([CH2:13][OH:14])[CH2:10][C:11]1=[O:12])=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 20467711HCID 20467711, compound

Product 1

HCID 54399885HCID 54399885, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.5 g. (18.5 mmoles) of ethyl 1-(2-ethoxycarbonylethyl)-4-oxo-2-azetidine-carboxylate prepared according to Example 4 are dissolved in 20 ml. of dry ethanol, whereupon 1.4 g. (37 mmoles) of sodium tetrahydroborate(III) are added to the solution at 0° C., with stirring. The reaction mixture is stirred for an additional hour, and is then evaporated in vacuo, at room temperature. The residue is dissolved in 20 ml. of saturated aqueous hydrochloric acid solution and the pH of the solution is adjusted to 6.5 by addition of a 5% aqueous hydrochloric acid solution. The mixture is extracted with three 30-ml. portions of chloroform, dried with magnesium sulfate and filtered. The remaining solution is evaporated in vacuo. 3.1 g. (83%) of the named compound are obtained.

Workup

  1. dissolutionare dissolved in 20 ml
  2. stirringThe reaction mixture is stirred for an additional hour
  3. customis then evaporated in vacuo, at room temperature
  4. dissolutionThe residue is dissolved in 20 ml
  5. additionof saturated aqueous hydrochloric acid solution and the pH of the solution is adjusted to 6.5 by addition of a 5% aqueous hydrochloric acid solution
  6. extractionThe mixture is extracted with three 30-ml
  7. dry with materialportions of chloroform, dried with magnesium sulfate
  8. filtrationfiltered
  9. customThe remaining solution is evaporated in vacuo

Sources & evidence

ORD record
ord-b4e24b8714294350ae242d70ecef6d27
Source dataset
uspto-grants-1984_03
Patent number
US04435322

Reaction notes

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