Styrene → HCID 15867808, compound

HRID 1604115Notes

Reaction equation

HRID 1604115 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.B1C2CCCC1CCC2.FC(F)(F)S(O[C:24]1[CH2:38][C@@H:37]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[C@H:36](/[CH:47]=[CH:48]/[C@@H:49]([O:57][Si:58]([C:61]([CH3:64])([CH3:63])[CH3:62])([CH3:60])[CH3:59])[CH2:50][C@H:51]([CH3:56])[CH2:52][CH2:53][CH2:54][CH3:55])[C:25]=1[S:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])(=O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[O-][Si]([O-])=O.[Mg+2]>O1CCCC1>[CH2:1]([C:24]1[CH2:38][C@@H:37]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[C@H:36](/[CH:47]=[CH:48]/[C@@H:49]([O:57][Si:58]([C:61]([CH3:62])([CH3:63])[CH3:64])([CH3:60])[CH3:59])[CH2:50][C@H:51]([CH3:56])[CH2:52][CH2:53][CH2:54][CH3:55])[C:25]=1[S:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 7501StyreneHCID 61680MAGNESIUM SILICATE (synthetic)HCID 62657Potassium Phosphate, TribasicHCID 789669-Borabicyclo(3.3.1)nonaneHCID 15867790HCID 15867790, compound

Product 1

HCID 15867808HCID 15867808, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Styrene (150 μl, 1.0 mmol) in tetrahydrofuran (3 mL) was ice-cooled, then 9-BBN, (0.5M THF solution, 2.1 mL, 1.05 mmol) was added. This was agitated for 6 hours while gradually raising the reaction temperature to room temperature. Further, to this were added methyl (11R,12S,13E,15S,17R)-9-trifluoromethanesulfonyloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (233 mg, 0.3 mmol), bistriphenylphosphinepalladiumchloride (70 mg, 0.1 mmol), and tripotassium phosphate (255 mg, 1.2 mmol) in tetrahydrofuran (5 mL) suspension. The reaction mixture was agitated at 60° C. for 15 hours. The reaction solution was cooled, then subjected to Florisil column chromotography to remove the metal complexes. The obtained solution was concentrated under reduced pressure, then was purified by silica gel column chromotography (2 to 4% ethyl acetate/hexane) to obtain methyl (11R,12S,13E,15S,17R)-9-phenethyl-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (104 mg, 48%).

Workup

  1. temperaturecooled
  2. stirringThe reaction mixture was agitated at 60° C. for 15 hours
  3. temperatureThe reaction solution was cooled
  4. customto remove the metal complexes
  5. concentrationThe obtained solution was concentrated under reduced pressure
  6. customwas purified by silica gel column chromotography (2 to 4% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c3f4a1565db04b8886bec53476f51e19
Source dataset
uspto-grants-1999_11
Patent number
US05990346

Reaction notes

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