Boron trifluoride → HCID 56673701, compound

HRID 1469202Notes

Reaction equation

HRID 1469202 reaction equation
[OH:1][CH2:2][C@H:3]1[O:8][C:7](OC)([C:9]2[S:10][C:11]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH3:24])=[CH:18][CH:17]=3)=[C:12]([CH3:14])[CH:13]=2)[C@H:6]([OH:27])[C@@H:5]([OH:28])[C@@H:4]1[OH:29].C([SiH](CC)CC)C.B(F)(F)F>C(Cl)Cl.C(#N)C>[OH:1][CH2:2][C@@H:3]1[C@@H:4]([OH:29])[C@H:5]([OH:28])[C@@H:6]([OH:27])[C@H:7]([C:9]2[S:10][C:11]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][CH3:24])=[CH:20][CH:21]=3)=[C:12]([CH3:14])[CH:13]=2)[O:8]1

Participants

6

Reactant 3

HCID 6356Boron trifluorideHCID 12052TriethylsilaneHCID 66691101HCID 66691101, compound

Product 1

HCID 56673701HCID 56673701, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-45 °C

Procedure

To a solution of crude (3R,4S,5S,6R)-6-(hydroxymethyl)-2-methoxy-2-(4-methyl-5-(4-propylbenzyl)thiophen-2-yl)tetrahydro-2H-pyran-3,4,5-triol (50) in DCM (11.8 mL) and ACN (11.8 mL) was added triethylsilane (0.786 mL, 4.90 mmol) followed by BF3 etherate (0.611 mL, 4.90 mmol) under nitrogen atmosphere at −60° C. The reaction temperature was maintained −60 to −30° C. for 2 hours. The reaction was quenched with a saturated NaHCO3 solution (20 mL), and then extracted with EtOAc (50 mL). The organic phase was dried over MgSO4 and evaporated under vacuum. The residue was further purified by prep HPLC (C18) to provide the title compound 51 (391 mg, 0.996 mmol, 37%).

Workup

  1. customThe reaction was quenched with a saturated NaHCO3 solution (20 mL)
  2. extractionextracted with EtOAc (50 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. customevaporated under vacuum
  5. customThe residue was further purified by prep HPLC (C18)

Sources & evidence

ORD record
ord-dfd95b96c3304f9e8984031439f96a96
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

Loading…