Triethylamine → HCID 22262198, compound

HRID 1610260Notes

Reaction equation

HRID 1610260 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[C:15]2[CH:16](O)[CH:17]([CH3:21])[CH2:18][CH2:19][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]=[C:17]([CH3:21])[CH2:18][CH2:19][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 22261859HCID 22261859, compound

Product 1

HCID 22262198HCID 22262198, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 4-[[[tert-butyl(dimethyl)silyl]oxy]methyl]-6-methyl-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-ol (14.43 g, 45.02 mmol), triethylamine (7.53 ml, 54.0 mmol) and 4-N,N-dimethylaminopyridine (0.55 g, 4.50 mmol) in acetonitrile (50 ml) was dropwise added a solution of methanesulfonyl chloride (5.67 g, 49.5 mmol) in acetonitrile (10 ml) under ice-cooling. Lithium chloride (2.86 g, 67.5 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 collected 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 (50 ml). 1,8-Diazabicyclo[5.4.0]-7-undecene (13.5 ml, 90.0 mmol) was added and the mixture was stirred overnight at 80° C. The reaction solution was poured into water and extracted twice with ethyl acetate. The collected 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=50/1) to give the objective substance.

Workup

  1. temperaturecooling
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe collected 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 (50 ml)
  6. stirringthe mixture was stirred overnight at 80° C
  7. extractionextracted twice with ethyl acetate
  8. dry with materialThe collected 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=50/1)
  12. customto give the objective substance

Sources & evidence

ORD record
ord-75163332c3e946fcad8bafa585335b8e
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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