Trimethylsilyl triflate → HCID 44237860, compound

HRID 2064527Notes

Reaction equation

HRID 2064527 reaction equation
C[Si](OS(C(F)(F)F)(=O)=O)(C)C.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][CH2:23][CH2:24][C:25]2(O)[CH2:30][CH2:29][C:28]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([N:31]([CH3:33])[CH3:32])[CH2:27][CH2:26]2)=[CH:14]1>ClCCl>[CH2:34]([C:28]1([N:31]([CH3:33])[CH3:32])[CH2:29][CH2:30][C:25]2([C:14]3[NH:13][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]=3[CH2:22][CH2:23][CH2:24]2)[CH2:26][CH2:27]1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 65367Trimethylsilyl triflateHCID 68640828HCID 68640828, compound

Product 1

HCID 44237860HCID 44237860, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoromethane sulphonic acid trimethylsilyl ester (1.30 mL, 1.59 g, 7.16 mmol) was added to a solution of 1-(3-(1H-indol-3-yl)propyl)-4-benzyl-4-(dimethylamino)cyclohexanol (700 mg, 1.79 mmol) in anhydrous dichloromethane (30 mL) and stirred for 2 d at room temperature. The reaction mixture was then diluted with dichloromethane (10 mL), and firstly washed with 1 N sodium carbonate solution (2×10 mL), then with water and saturated sodium chloride solution (10 mL each), dried with sodium sulphate and concentrated to low volume in a vacuum. The residue was taken up in methanol (30 mL), stirred over the weekend at room temperature and decanted off from the separated precipitate (fraction 1). The solution was concentrated to low volume, the residue taken up in methanol (2×10 mL) and decanted off from the precipitated solid again in each case. The remaining solution was concentrated to low volume in a vacuum, as a result of which fraction 2 was obtained.

Workup

  1. washfirstly washed with 1 N sodium carbonate solution (2×10 mL)
  2. dry with materialwith water and saturated sodium chloride solution (10 mL each), dried with sodium sulphate
  3. concentrationconcentrated to low volume in a vacuum
  4. stirringstirred over the weekend at room temperature
  5. customdecanted off from the separated precipitate (fraction 1)
  6. concentrationThe solution was concentrated to low volume
  7. customdecanted off from the precipitated solid again in each case
  8. concentrationThe remaining solution was concentrated to low volume in a vacuum
  9. customas a result of which fraction 2
  10. customwas obtained

Sources & evidence

ORD record
ord-0c2aafa8a3e24651a1c7f6f63442143e
Source dataset
uspto-grants-2012_10
Patent number
US08288430B2

Reaction notes

Loading…