Hydrochloric Acid → HCID 19043220, compound

HRID 1901099Notes

Reaction equation

HRID 1901099 reaction equation
[CH2:1]([NH:4][CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].C1(C)C=C[C:11]([S:14](O)(=O)=O)=[CH:10][CH:9]=1.C([BH3-])#N.[Na+].[ClH:23].[OH-].[Na+].[C:26]1([CH3:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1.O>[ClH:23].[CH2:1]([N:4]([CH2:5][CH2:6][CH3:7])[CH:10]1[CH2:9][C:31]2[C:30](=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:32])[S:14][CH2:11]1)[CH2:2][CH3:3]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 8902DipropylamineHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 19043220HCID 19043220, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Part H (620 mg, 2.73 mMol) in toluene (20 mL) were added dipropylamine (0.7 mL, 6 mMol) and p-toluenesulfonic acid (100 mg, 0.52 mMol), and the mixture was heated at reflux with constant water removal (Dean-Stark trap). After 3 hours the reaction mixture was cooled to room temperature and the volatiles removed in vacuo to give a dark reddish-orange residue. This material was dissolved in tetrahydrofuran (40 mL), sodium cyanoborohydride (400 mg, 6.4 mMol) was added and the solution was saturated with hydrogen chloride. The reaction mixture was stirred for 18 hours at room temperature. The reaction mixture was then poured into 15% sodium hydroxide (100 mL) and was stirred vigorously for 2 hours. The reaction mixture was then extracted well with diethyl ether. The organic phases were combined, dried over sodium sulfate, and concentrated in vacuo. The residue was suspended in 10% hydrochloric acid and the aqueous extracted once with diethyl ether. This ether extract was discarded and the remaining aqueous made basic with concentrated ammonium hydroxide and then extracted well with dichloromethane. The combined organics were washed with saturated aqueous sodium chloride, dried over sodium sulfate, and concentrated in vacuo to give a light yellow oil. Purification by flash chromatography (4:1 hexane:diethyl ether+tr. NH4OH) gave the title compound as a colorless oil (420 mg, 50%).

Workup

  1. temperaturethe mixture was heated
  2. customthe volatiles removed in vacuo
  3. customto give a dark reddish-orange residue
  4. stirringwas stirred vigorously for 2 hours
  5. extractionThe reaction mixture was then extracted well with diethyl ether
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. extractionthe aqueous extracted once with diethyl ether
  9. extractionThis ether extract
  10. extractionextracted well with dichloromethane
  11. washThe combined organics were washed with saturated aqueous sodium chloride
  12. dry with materialdried over sodium sulfate
  13. concentrationconcentrated in vacuo
  14. customto give a light yellow oil
  15. customPurification by flash chromatography (4:1 hexane:diethyl ether+tr. NH4OH)

Sources & evidence

ORD record
ord-b23548254a6a40dcbcffbffb79a4c749
Source dataset
uspto-grants-1996_11
Patent number
US05576352

Reaction notes

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