Methanol → HCID 23453188, compound

HRID 1277688Notes

Reaction equation

HRID 1277688 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1([CH2:14][OH:15])[CH:10]([OH:11])[CH:9]([OH:12])[CH:8]([OH:13])[CH2:7][NH:6]1.CO.C(N(CC)CC)C.[CH2:25]([O:31][C:32](Cl)=[O:33])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>O.C(OCC)(=O)C>[CH2:25]([O:31][C:32]([NH:3][CH2:4][C:5]1([CH2:14][OH:15])[CH:10]([OH:11])[CH:9]([OH:12])[CH:8]([OH:13])[CH2:7][NH:6]1)=[O:33])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 22466Hexyl chloroformateHCID 20449506HCID 20449506, compound

Product 1

HCID 23453188HCID 23453188, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.3 g of 2-aminomethyl-2-hydroxymethyl-3,4,5-trihydroxypiperidine dihydrochloride (Example 11) are dissolved in 20 ml of water, and 30 ml of methanol and 8.4 ml of triethylamine are added. 7.8 ml of chloroformic acid hexyl ester, dissolved in 30 ml of ethyl acetate are added dropwise to this solution at 0°-5° C. After stirring the mixture at room temperature for three hours, it is concentrated. The evaporation residue is partitioned in water/ethyl acetate, the phases are separated and the ethyl acetate phase is washed 1× with water. The combined aqueous phases are stirred with 80 g of Amberlite IR A 400, OH- form for 1 hour, the mixture is filtered and the filtrate is concentrated. The evaporation residue is dissolved in a little methanol and the solution is discharged onto a column 120 cm long and 4 cm wide which contains cellulose as the stationary phase and acetone as the mobile phase. The column is washed with acetone. The substance is obtained by elution with 95% pure acetone. After concentrating the eluate, 2.4 g of an almost colourless yellow foam are obtained.

Workup

  1. additionare added dropwise to this solution at 0°-5° C
  2. concentrationit is concentrated
  3. customThe evaporation residue is partitioned in water/ethyl acetate
  4. customthe phases are separated
  5. washthe ethyl acetate phase is washed 1× with water
  6. stirringThe combined aqueous phases are stirred with 80 g of Amberlite IR A 400, OH- form for 1 hour
  7. filtrationthe mixture is filtered
  8. concentrationthe filtrate is concentrated
  9. dissolutionThe evaporation residue is dissolved in a little methanol
  10. washThe column is washed with acetone
  11. customThe substance is obtained by elution with 95% pure acetone
  12. concentrationAfter concentrating the eluate, 2.4 g of an almost colourless yellow foam
  13. customare obtained

Sources & evidence

ORD record
ord-e768d6535338403f96cb8d002f48eafc
Source dataset
uspto-grants-1981_07
Patent number
US04278683

Reaction notes

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