Pyridine → HCID 14134382, compound

HRID 1651663Notes

Reaction equation

HRID 1651663 reaction equation
[O:1]([CH2:9][C@H:10]1[C@H:15]([OH:16])[CH2:14][O:13][C@@H:12]([CH3:17])[O:11]1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].N1C=CC=CC=1.FC(F)(F)C(O)=O.C1(N=C=NC2CCCCC2)CCCCC1>C1C=CC=CC=1.CS(C)=O.O.C(OCC)(=O)C>[O:1]([CH2:9][C@H:10]1[C:15](=[O:16])[CH2:14][O:13][C@@H:12]([CH3:17])[O:11]1)[Si:2]([C:5]([CH3:8])([CH3:6])[CH3:7])([CH3:4])[CH3:3]

Participants

9

Reactant 4

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 14134379HCID 14134379, compound

Product 1

HCID 14134382HCID 14134382, compoundYield 77.3%

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2R,4S,5R)-4-t-butyldimethylsiloxymethyl-5-hydroxy-2-methyl-1,3-dioxane (4.2 g) in a mixture of benzene (30 ml) and dimethylsulfoxide (5.7 ml) were added pyridine (1.30 ml), trifluoroacetic acid (0.62 ml) and N,N'-dicyclohexylcarbodiimide (9.90 g) under cooling in an ice bath and the mixture was stirred at room temperature for 3 hours. The resulting solution were added ethyl acetate (50 ml) and water (30 ml) and stirred for 30 minutes. After removal of insoluble urea by filtration, the organic layer was separated and washed successively with water and brine. The solution was dried over magnesium sulfate and the solvent was evaporated in vacuo to give crude oil. The oil was purified with silica gel column (50 g) (n-hexane : ethyl acetate=10:1) to give (2R,4S) 4 t-butyldimethylsiloxymethyl-2-methyl-1,3-dioxan-5-one (3.22 g) as a pale yellow oil.

Workup

  1. temperatureunder cooling in an ice bath
  2. stirringstirred for 30 minutes
  3. customAfter removal of insoluble urea
  4. filtrationby filtration
  5. customthe organic layer was separated
  6. washwashed successively with water and brine
  7. dry with materialThe solution was dried over magnesium sulfate
  8. customthe solvent was evaporated in vacuo
  9. customto give crude oil
  10. customThe oil was purified with silica gel column (50 g) (n-hexane : ethyl acetate=10:1)

Sources & evidence

ORD record
ord-0ae9f56d9131414aa944d461bdc99657
Source dataset
uspto-grants-1990_05
Patent number
US04929639

Reaction notes

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