1-Pentene → HCID 15867799, compound

HRID 1604110Notes

Reaction equation

HRID 1604110 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH3:5].[CH:6]12BC(CCC1)CCC2.C[CH:16]([CH2:20][CH2:21][CH2:22][CH2:23][S:24][C:25]1[C@@H:29](/[CH:30]=[CH:31]/[C@@H:32]([O:40][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42])[CH2:33][C@H:34]([CH3:39])[CH2:35][CH2:36][CH2:37][CH3:38])[C@H:28]([O:48][Si:49]([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50])[CH2:27]C=1OS(C(F)(F)F)(=O)=O)[C:17]([OH:19])=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[O-][Si]([O-])=O.[Mg+2].[O:77]1CCC[CH2:78]1>>[CH2:2]([C:1]1[CH2:27][C@@H:28]([O:48][Si:49]([C:52]([CH3:54])([CH3:53])[CH3:55])([CH3:50])[CH3:51])[C@H:29](/[CH:30]=[CH:31]/[C@@H:32]([O:40][Si:41]([C:44]([CH3:45])([CH3:47])[CH3:46])([CH3:42])[CH3:43])[CH2:33][C@H:34]([CH3:39])[CH2:35][CH2:36][CH2:37][CH3:38])[C:25]=1[S:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:16][C:17]([O:77][CH3:78])=[O:19])[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 6

HCID 80041-PenteneHCID 8028Tetrahydrofuran2×HCID 61680MAGNESIUM SILICATE (synthetic)HCID 62657Potassium Phosphate, TribasicHCID 789669-Borabicyclo(3.3.1)nonaneHCID 86754854HCID 86754854, compound

Product 1

HCID 15867799HCID 15867799, compoundYield 38%

Procedure

1-pentene (110 μl, 1.0 mmol) in tetrahydrofuran (3 mL) was ice-cooled, then 9-borabicyclo[3,3,1]nonane (9-BBN, 0.5M THF solution, 2.0 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-dienoic acid (205 mg, 0.264 mmol), bistriphenylphosphinepalladiumchloride (140 mg, 0.2 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 resultant 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-pentyl-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (71 mg, 38%).

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 resultant 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-24f587d066a6426aae77f8aa305c5b36
Source dataset
uspto-grants-1999_11
Patent number
US05990346

Reaction notes

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