Acetic Anhydride → 4-Acetoxy-5-acetoxymethyl-1-acetyl-3-piperidinol

HRID 1003378Notes

Reaction equation

HRID 1003378 reaction equation
C([O:8][C@H:9]1[C@H:14]([OH:15])[C@@H:13]([CH2:16][OH:17])[CH2:12][NH:11][CH2:10]1)C1C=CC=CC=1.C(O[C:22](=[O:24])[CH3:23])(=O)C>N1C=CC=CC=1>[C:9]([O:15][CH:14]1[CH:13]([CH2:16][O:17][C:14](=[O:15])[CH3:13])[CH2:12][N:11]([C:22](=[O:24])[CH3:23])[CH2:10][CH:9]1[OH:8])(=[O:8])[CH3:10]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15235481(3R,4R,5R)-3-Benzyloxy-5-hydroxymethyl4-piperidinol

Product 1

HCID 187970934-Acetoxy-5-acetoxymethyl-1-acetyl-3-piperidinolYield 55%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(3R,4R,5R)-3-Benzyloxy-5-hydroxymethyl4-piperidinol (0.1 g, 0.4 mmol) was dissolved in pyridine (0.5 ml) at 0° C. by and acetic anhydride (0.5 ml) was added dropwise over 1 min. Stirring at room temperature for 20 h and evaporation to dryness gave a crude product which was purified on silica gel using ethanol as eluent (yield 55%). The purified 3-benzyloxy-3-acetoxy-5-acetoxymethyl-1-acetylpiperidine (75 mg) was debenzylated in methanol at room temperature using 10% Pd/C as catalyst. Filtration and evaporation to dryness gave 50 mg of crude 4-acetoxy-5-acetoxymethyl-1-acetyl-3-piperidinol which was dissolved in dry methanol (4 ml) containing 50 μl of a 1% sodium methoxide in methanol. After stirring at room temperature for 4 days the solution was evaporated to dryness to give (3R,4R,5R)-1-acetyl-5-hydroxymethyl-3,4-piperidinediol (Yield: 35 mg).

Workup

  1. additionwas added dropwise over 1 min
  2. customevaporation to dryness
  3. customgave a crude product which
  4. customwas purified on silica gel
  5. customwas debenzylated in methanol at room temperature
  6. filtrationFiltration and evaporation to dryness

Sources & evidence

ORD record
ord-34b755502748409c84d0e47c84d03be9
Source dataset
uspto-grants-2000_04
Patent number
US06046214

Reaction notes

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