HCID 86588181, compound → (3R,4S,5R)-5-(5-Ethyl-3-isoxazolyl)tetrahydro-2,3,4-furantriol

HRID 2297674Notes

Reaction equation

HRID 2297674 reaction equation
C[O:2][C@H:3]1[C@@H:7]2[O:8]C(C)(C)[O:10][C@@H:6]2[C@@H:5]([C:13](=[N:19][OH:20])[CH2:14][C:15](=O)[CH2:16][CH3:17])[O:4]1>C(O)(=O)C>[CH2:16]([C:15]1[O:20][N:19]=[C:13]([C@H:5]2[O:4][CH:3]([OH:2])[C@H:7]([OH:8])[C@@H:6]2[OH:10])[CH:14]=1)[CH3:17]

Participants

3

Reactant 1

HCID 86588181HCID 86588181, compound

Product 1

HCID 45093395(3R,4S,5R)-5-(5-Ethyl-3-isoxazolyl)tetrahydro-2,3,4-furantriolYield 40.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

1-[(3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]pentane-1,3-dione 1-oxime (0.5 g) was dissolved in aqueous acetic acid (18 mg) and the mixture heated at 100° C. for 2 h. The solution was cooled and concentrated in vacuo to afford a brown oil which was azeotroped with toluene. Purification by chromatography on silica gel (Varian Bondelut silica gel cartridge), eluting with (i) dichloromethane, (ii) ether, (iii) ethyl acetate, (iv) methanol, gave the title compound (150 mg).

Workup

  1. temperatureThe solution was cooled
  2. concentrationconcentrated in vacuo
  3. customto afford a brown oil which
  4. customwas azeotroped with toluene
  5. customPurification by chromatography on silica gel (Varian Bondelut silica gel cartridge)
  6. washeluting with (i) dichloromethane, (ii) ether, (iii) ethyl acetate, (iv) methanol

Sources & evidence

ORD record
ord-39bcedba648a4da79b3467006d4d6c83
Source dataset
uspto-grants-2002_12
Patent number
US06492348B1

Reaction notes

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