Trifluoroacetic acid → HCID 14606665, compound

HRID 893609Notes

Reaction equation

HRID 893609 reaction equation
CO[CH:3]([O:10]C)[C@@H:4]1[O:8][CH2:7][C@@H:6]([OH:9])[CH2:5]1.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O-])(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(C(O)=O)(F)(F)F.[OH-].[Na+].[BH4-].[Na+]>O1CCOCC1>[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O:9][C@@H:6]2[CH2:7][O:8][C@@H:4]([CH2:3][OH:10])[CH2:5]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 86745953HCID 86745953, compound

Product 1

HCID 14606665HCID 14606665, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (3S-trans)-tetrahydro-5-(dimethoxymethyl)-3-furanol-4-methylbenzenesulfonate, (Compound IV(e), 10.0 g, 31.6 mmole), 1% CF3CO2H (50 mL), and dioxane (80 mL) in a 250 mL round bottom flask fitted with a reflux condenser was warmed to 80° C. for five hours. After cooling to room temperature, the solution was adjusted to pH 7.0 using 1N NaOH, treated with NaBH4 (1.2 g, 31.7 mmole), and allowed to stir at room temperature for an additional 30 minutes. The solvent was partially removed, then extracted with EtOAc (100 mL×3). The organic fraction was dried over MgSO4, filtered, evaporated and purified by flash column chromatorgraphy (60% EtOAc/40% Hexane) to afford 3.6 g or recovered starting material and 2.7 g (49% based on recovered starting material) of Compound IV(c).

Workup

  1. customfitted with a reflux condenser
  2. temperatureAfter cooling to room temperature
  3. customThe solvent was partially removed
  4. extractionextracted with EtOAc (100 mL×3)
  5. dry with materialThe organic fraction was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. custompurified by flash column chromatorgraphy (60% EtOAc/40% Hexane)
  9. customto afford 3.6 g
  10. customrecovered
  11. custommaterial and 2.7 g (49% based on recovered starting material) of Compound IV(c)

Sources & evidence

ORD record
ord-32006c7b986c4262be99a978949e5dec
Source dataset
uspto-grants-1992_06
Patent number
US05126347

Reaction notes

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