1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 18539170, compound

HRID 412901Notes

Reaction equation

HRID 412901 reaction equation
CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)(=O)=O.[N:19]1[C:27]2[N:22]3[C:23](=[N:28][CH:29]=[C:21]3[C:20]=1[SH:30])[CH:24]=[CH:25][CH:26]=2.C1CCN2C(=NCCC2)CC1>CN(C=O)C>[N:19]1[C:27]2[N:22]3[C:23](=[N:28][CH:29]=[C:21]3[C:20]=1[S:30][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11]1)[CH:24]=[CH:25][CH:26]=2

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 178527767HCID 178527767, compound

Product 1

HCID 18539170HCID 18539170, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 4-[(methylsulfonyl)oxy]-1-piperidinecarboxylate (3.5 g, 12.5 mmol) in DMF (60 ml) were added 1,4,7b-triazacyclopenta[cd]inden-2-thiol (3.7 g, 21.3 mmol). and DBU (3.7 ml, 25 mmol), and the mixture was stirred at 80° C. for 11 hours. The reaction mixture was concentrated under reduced pressure, and to the concentrate was added water (200 ml). The mixture was extracted with a mixed solution of THF and ethyl acetate (3/2, 500 ml). The organic layer was washed with saturated aqueous solution of sodium chloride (200 ml), successively, and dried over anhydrous sodium sulfate, concentrated under reduced pressure. The concentrate was subjected to flash column chromatography (silica gel 30 g,: ethyl acetate/hexane=1/2 to 1/0), and the desired fraction was concentrated under reduced pressure. To the concentrate was added diisopropyl ether and the precipitates were collected by filtration to give the titled compound (2.5 g, 7 mmol) as yellowish powdery crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the concentrate was added water (200 ml)
  3. extractionThe mixture was extracted with a mixed solution of THF and ethyl acetate (3/2, 500 ml)
  4. washThe organic layer was washed with saturated aqueous solution of sodium chloride (200 ml)
  5. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. concentrationthe desired fraction was concentrated under reduced pressure
  8. additionTo the concentrate was added diisopropyl ether
  9. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-10e805b75892486d9e12d95ce5e49435
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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