Trimethylsilyl triflate → 6-fluoro-N,N-dimethyl-4'-phenyl-2,3,4,9-tetrahydrospiro[carbazole-1,1'-cyclohexane]-4'-amine

HRID 2064521Notes

Reaction equation

HRID 2064521 reaction equation
C[Si](OS(C(F)(F)F)(=O)=O)(C)C.[CH3:13][N:14]([CH3:41])[C:15]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:20][CH2:19][C:18]([CH2:22][CH2:23][CH2:24][C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([F:34])[CH:32]=3)[NH:27][CH:26]=2)(O)[CH2:17][CH2:16]1>ClCCl>[F:34][C:31]1[CH:32]=[C:33]2[C:28](=[CH:29][CH:30]=1)[NH:27][C:26]1[C:18]3([CH2:19][CH2:20][C:15]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)([N:14]([CH3:41])[CH3:13])[CH2:16][CH2:17]3)[CH2:22][CH2:23][CH2:24][C:25]2=1

Participants

4

Reactant 2

HCID 65367Trimethylsilyl triflateHCID 689159774-dimethylamino-1-[3-(5-fluoro-1H-indol-3-yl)propyl]-4-phenylcyclohexanol

Product 1

HCID 689155776-fluoro-N,N-dimethyl-4'-phenyl-2,3,4,9-tetrahydrospiro[carbazole-1,1'-cyclohexane]-4'-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoromethane sulphonic acid trimethylsilyl ester (822 mg, 671 μL, 3.70 mmol) was added to a suspension of 4-dimethylamino-1-[3-(5-fluoro-1H-indol-3-yl)propyl]-4-phenyl-cyclohexanol (365 mg, 0.92 mmol) in absolute dichloromethane (50 mL), and stirred for 10 d at room temperature. The reaction solution was then diluted with dichloromethane (10 mL), washed with 1 N sodium carbonate solution (2×10 mL), water and saturated sodium chloride solution (10 mL each), the organic phase dried with sodium sulphate and concentrated to low volume in a vacuum. The residue (249 mg) was mixed with methanol (50 mL) and stirred over the weekend at room temperature, wherein a light-coloured solid formed, which was filtered off and washed with a little methanol (2 mL).

Workup

  1. washwashed with 1 N sodium carbonate solution (2×10 mL), water and saturated sodium chloride solution (10 mL each)
  2. dry with materialthe organic phase dried with sodium sulphate
  3. concentrationconcentrated to low volume in a vacuum
  4. additionThe residue (249 mg) was mixed with methanol (50 mL)
  5. stirringstirred over the weekend at room temperature
  6. customwherein a light-coloured solid formed
  7. filtrationwhich was filtered off
  8. washwashed with a little methanol (2 mL)

Sources & evidence

ORD record
ord-78f0ede6ee5348ffa53c000fb4e94e40
Source dataset
uspto-grants-2012_10
Patent number
US08288430B2

Reaction notes

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