Methanol → HCID 18761510, compound

HRID 1702593Notes

Reaction equation

HRID 1702593 reaction equation
[C:1](Cl)(=[O:8])C1C=CC=CC=1.CO.C(N(CC)CC)C.[C:19]([N:27]1[CH2:32][CH:31]([OH:33])[CH:30]([OH:34])[CH:29]([OH:35])[CH2:28]1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)(=O)C.O>[C:19]([N:27]1[CH2:28][CH:29]([OH:35])[CH:30]([OH:34])[CH:31]([OH:33])[CH:32]1[CH2:1][OH:8])(=[O:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 7412Benzoyl chloride2×HCID 8471Triethylamine2×HCID 20525971HCID 20525971, compound

Product 1

HCID 18761510HCID 18761510, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

27 ml of benzoyl chloride in 300 ml of ethyl acetate were added dropwise to a solution of 30 g of 1-desoxynojirimicin in 120 ml of H2O, 350 ml of CH3OH and 30 ml of triethylamine at 30°-35° C. The mixture was subsequently stirred at room temperature for 1 hour and a further 15 ml of triethylamine and 13.5 ml of benzoyl chloride in 150 ml of ethyl acetate were then added dropwise at 30°-35° C. After stirring for 1 hour, the reaction mixture was evaporated to dryness in vacuo. The residue was taken up in water and the aqueous mixture was extracted with ether. The aqueous phase was again concentrated to dryness in vacuo and the residue was stirred with acetone. The triethylamine hydrochloride which has precipitated was filtered off. Residual triethylamine hydrochloride was separated off by again concentrating the acetone solution and taking up the residue in a little acetone. After removal of the solvent, the product was obtained as a resin. After thorough drying, this resin could be employed in the next stage. Yield: 56 g of crude N-benzoyl-3,4,5-trihydroxypiperidine. After standing for a relatively long period, the compound crystallised from acetone. Melting point: 159° C.

Workup

  1. stirringAfter stirring for 1 hour
  2. customthe reaction mixture was evaporated to dryness in vacuo
  3. extractionthe aqueous mixture was extracted with ether
  4. concentrationThe aqueous phase was again concentrated to dryness in vacuo
  5. stirringthe residue was stirred with acetone
  6. customThe triethylamine hydrochloride which has precipitated
  7. filtrationwas filtered off
  8. customResidual triethylamine hydrochloride was separated off
  9. concentrationby again concentrating the acetone solution
  10. customAfter removal of the solvent
  11. customthe product was obtained as a resin
  12. waitAfter standing for a relatively long period
  13. customthe compound crystallised from acetone

Sources & evidence

ORD record
ord-9454e1363a0143a4aef84da3f9406bea
Source dataset
uspto-grants-1982_09
Patent number
US04348402

Reaction notes

Loading…