Acetonitrile → HCID 70272020, compound

HRID 1604123Notes

Reaction equation

HRID 1604123 reaction equation
C(#N)C.N1C=CC=CC=1.F.[O:11]([C@@H:19]1[CH2:23][C:22]([CH3:24])=[C:21]([S:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C@H:20]1/[CH:32]=[CH:33]/[CH:34]([O:42][Si](C(C)(C)C)(C)C)[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[Si](C(C)(C)C)(C)C>N1C=CC=CC=1>[CH2:26]([S:25][C:21]1[C@@H:20](/[CH:32]=[CH:33]/[CH:34]([OH:42])[CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C@H:19]([OH:11])[CH2:23][C:22]=1[CH3:24])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 64774Pyridine, hydrofluoride (1:1)HCID 70270863HCID 70270863, compound

Product 1

HCID 70272020HCID 70272020, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of ice-cooled acetonitrile (2 ml) and pyridine (0.5 mL) was added hydrogen fluoride-pyridine (0.5 mL). To this solution was added (3S,4R)-4-(tert-butyldimethylsiloxy)-2-hexylthio-3-[(1E)-4-phenyl-3-(tert-butyldimethylsiloxy)-1-butenyl]-1-methyl-1-cyclopentene (295 mg) in pyridine (1.5 mL). The ice bath was removed and the solution was agitated for 20 hours while returning it to room temperature. The reaction solution was poured into a mixture of ethyl acetate and saturated aqueous sodium hydrogencarbonate. The desired product was extracted from this mixed solution with ethyl acetate and was washed with brine, then was dried over anhydrous sodium sulfate. This was concentrated under reduced pressure, then was purified by silica gel column chromatography (30% ethyl acetate/hexane) to obtain stereoisomers of (3S,4R)-2-hexylthio-4-hydroxy-3-[(1E)-4-phenyl-3-hydroxy-1-butenyl]-1-methyl-1-cyclopentene separately (less polar compounds: 48.6 mg, 27%; more polar compounds: 53.5 mg, 30%).

Workup

  1. customThe ice bath was removed
  2. customto room temperature
  3. additionThe reaction solution was poured into a mixture of ethyl acetate and saturated aqueous sodium hydrogencarbonate
  4. extractionThe desired product was extracted from this mixed solution with ethyl acetate
  5. washwas washed with brine
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. concentrationThis was concentrated under reduced pressure
  8. customwas purified by silica gel column chromatography (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8a22bef666ae4450a2f5c67301ca8934
Source dataset
uspto-grants-1999_11
Patent number
US05990346

Reaction notes

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