Boron trifluoride etherate → HCID 86714022, compound

HRID 576307Notes

Reaction equation

HRID 576307 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[C:22]1(OC)[C@H:27]([OH:28])[C@@H:26]([OH:29])[C@H:25]([OH:30])[C@@H:24]([CH2:31][OH:32])[O:23]1)[CH:2]=[CH2:3].C([SiH](CC)CC)C.B(F)(F)F.CCOCC.C([O-])(O)=O.[Na+]>C(Cl)Cl.CC#N>[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[CH:22]1[C@H:27]([OH:28])[C@@H:26]([OH:29])[C@H:25]([OH:30])[C@@H:24]([CH2:31][OH:32])[O:23]1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 86714023HCID 86714023, compound

Product 1

HCID 86714022HCID 86714022, compound

Reagents, catalysts & solvents 1

HCID 21877088Acetonitrile methylene chlorideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of crude compound 23 (7.14 g 14.4 mmol) in CH2Cl2/CH3CN (75 mL/75 mL) were added triethylsilane (4.6 mL, 28.9 mmol) and boron trifluoride diethyl etherate (3.6 mL, 28.9 mmol) at −55° C. The mixture was allowed to slowly warm to 0° C. To a mixture was added aq. saturated NaHCO3 solution (75 mL) to quench the reaction and the mixture was evaporated in vacuo to remove CH2Cl2 and CH3CN. The mixture was extracted with EtOAc (100 mL×2). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude (3R,4R,5S,6R)-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (24, 6.36 g) was carried on to the next step without further purification.

Workup

  1. customto quench
  2. customthe reaction
  3. customthe mixture was evaporated in vacuo
  4. customto remove CH2Cl2 and CH3CN
  5. extractionThe mixture was extracted with EtOAc (100 mL×2)
  6. dry with materialThe combined organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude (3R,4R,5S,6R)-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (24, 6.36 g) was carried on to the next step without further purification

Sources & evidence

ORD record
ord-37e15afc0f9e4f0dbf260ea9458815fd
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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