Triethylamine → HCID 86593288, compound

HRID 1610660Notes

Reaction equation

HRID 1610660 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[C:15]2[CH:16](O)[CH2:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH2:20][C:14]=2[CH:13]=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[Cl-].[Li+].C1CCN2C(=NCCC2)CC1>C(#N)C.O>[C:4]([Si:1]([O:8][CH2:9][C:10]1[C:15]2[CH:16]=[CH:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH2:20][C:14]=2[CH:13]=[CH:12][CH:11]=1)([CH3:3])[CH3:2])([CH3:7])([CH3:5])[CH3:6]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 433294Lithium ChlorideHCID 22262278HCID 22262278, compound

Product 1

HCID 86593288HCID 86593288, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 4-[[[tert-butyl(dimethyl)silyl]oxy]methyl]-8,8-dimethyl-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-ol (28.90 g, 86.38 mmol), triethylamine (24.1 ml, 173 mmol) and 4-N,N-dimethylaminopyridine (1.06 g, 8.64 mmol) in acetonitrile (100 ml) was dropwise added a solution of methanesulfonyl chloride (14.8 g, 130 mmol) in acetonitrile (10 ml) under ice-cooling. Lithium chloride (5.49 g, 130 mmol) was added thereto, and the mixture was stirred at room temperature for 6 hrs. The reaction solution was poured into water and extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in N,N-dimethylformamide (100 ml), and 1,8-diazabicyclo[5.4.0]-7-undecene (25.8 ml, 173 mmol) was added. The mixture was stirred at 80° C. overnight. The reaction solution was-poured into water and extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1) to give the objective substance.

Workup

  1. temperaturecooling
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe recovered organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. dissolutionThe obtained residue was dissolved in N,N-dimethylformamide (100 ml)
  6. stirringThe mixture was stirred at 80° C. overnight
  7. extractionextracted twice with ethyl acetate
  8. dry with materialThe recovered organic layer was dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe obtained crude product
  11. customwas purified by silica gel column chromatography (hexane/ethyl acetate=15/1)
  12. customto give the objective substance

Sources & evidence

ORD record
ord-a09ee5ebfe0643ad914eb69d4f10e4a1
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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