Triethylsilane → HCID 57809578, compound

HRID 628759Notes

Reaction equation

HRID 628759 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(OC)[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][OH:18])[O:9]2)=[CH:4][C:3]=1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C([SiH](CC)CC)C>C(Cl)Cl.C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][OH:18])[O:9]2)=[CH:4][C:3]=1[CH2:21][C:22]1[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 11955530(3R,4S,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Product 1

HCID 57809578HCID 57809578, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

The crude (3R,4S,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (6.5 g) and triethyl silane (4.03 g, 34.7 mmol) were dissolved in a mixed solvent of methylene chloride (100 mL) and acetonitrile (100 mL). To the resulting mixture was added dropwise boron trifluoride-diethyl etherate complex (5.6 g, 39.5 mmol) at 0° C. After the completion of dropwise addition, the resulting mixture was warmed up to room temperature and stirred for 16 hr. The mixture was quenched with a saturated sodium bicarbonate solution, and extracted with ethyl acetate (250 mL×3). The organic phases were combined, washed with a saturated sodium chloride solution, dried over anhydrous sodium sulphate, and concentrated under a reduced pressure. The resulting crude product was purified with a silica-gel column chromatography (methanol:methylene chloride=0-1:15) to produce 3.8 g of a product in a yield of 46% (three steps in total).

Workup

  1. additionAfter the completion of dropwise addition
  2. customThe mixture was quenched with a saturated sodium bicarbonate solution
  3. extractionextracted with ethyl acetate (250 mL×3)
  4. washwashed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under a reduced pressure
  7. customThe resulting crude product was purified with a silica-gel column chromatography (methanol:methylene chloride=0-1:15)

Sources & evidence

ORD record
ord-81bb8553cba14f3097c27b38cbd46081
Source dataset
uspto-grants-2016_04
Patent number
US09315438B2

Reaction notes

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