Trimethylsilyl triflate → HCID 44237907, compound

HRID 2064531Notes

Reaction equation

HRID 2064531 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]([N:36]([CH3:38])[CH3:37])([C:31]3[S:32][CH:33]=[CH:34][CH:35]=3)[CH2:27][CH2:26]2)=[CH:14]1>ClCCCl>[CH3:37][N:36]([CH3:38])[C:28]1([C:31]2[S:32][CH:33]=[CH:34][CH:35]=2)[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

Participants

4

Reactant 2

HCID 65367Trimethylsilyl triflateHCID 68640619HCID 68640619, compound

Product 1

HCID 44237907HCID 44237907, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

Trifluoromethane sulphonic acid trimethylsilyl ester (1.95 g, 159 mL, 8.8 mmol) in absolute 1,2 dichloroethane (100 mL) was added to a suspension of 1-(3-(1H-indol-3-yl)propyl)-4-(dimethylamino)-4-(thiophen-2-yl)cyclohexanol (800 mg, 2.1 mmol), and a clear solution formed. The solution was stirred for 6 h at 50° C. and then overnight at room temperature. The reaction solution was washed with 1 N sodium carbonate solution (2×30 mL), water and saturated sodium chloride solution (30 mL each) one after the other, dried with sodium sulphate and concentrated to low volume in a vacuum. The raw product (720 mg) was mixed with methanol (100 mL) and stirred overnight at room temperature, during which a light-coloured solid was formed. This was filtered off, washed with methanol (10 mL) and dried in a vacuum, as a result of which a diastereomer mixture in a ratio of 5:1 was obtained (290 mg, (38%)). This was separated by preparative HPLC.

Workup

  1. customa clear solution formed
  2. customovernight
  3. customat room temperature
  4. washThe reaction solution was washed with 1 N sodium carbonate solution (2×30 mL), water and saturated sodium chloride solution (30 mL each) one after the other,
  5. dry with materialdried with sodium sulphate
  6. concentrationconcentrated to low volume in a vacuum
  7. additionThe raw product (720 mg) was mixed with methanol (100 mL)
  8. stirringstirred overnight at room temperature, during which a light-coloured solid
  9. customwas formed
  10. filtrationThis was filtered off
  11. washwashed with methanol (10 mL)
  12. customdried in a vacuum
  13. customas a result of which a diastereomer mixture in a ratio of 5:1
  14. customwas obtained (290 mg, (38%))
  15. customThis was separated by preparative HPLC

Sources & evidence

ORD record
ord-0681f8611bcd4c57a8e778c713207a62
Source dataset
uspto-grants-2012_10
Patent number
US08288430B2

Reaction notes

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