Dichloromethane → (S)-N,N,3-trimethyl-4'-phenyl-2,3,4,9-tetrahydrospiro[carbazole-1,1'-cyclohexane]-4'-amine

HRID 2064538Notes

Reaction equation

HRID 2064538 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@@H:11]([CH3:29])[CH2:12][C:13]2(O)[CH2:18][CH2:17][C:16]([N:25]([CH3:27])[CH3:26])([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)=[CH:2]1.C[Si](OS(C(F)(F)F)(=O)=O)(C)C.ClCCl>ClCCCl>[CH3:26][N:25]([CH3:27])[C:16]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][CH2:18][C:13]2([C:2]3[NH:1][C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[C:3]=3[CH2:10][C@@H:11]([CH3:29])[CH2:12]2)[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65367Trimethylsilyl triflateHCID 68640809(R)-1-(3-(1H-indol-3-yl)-2-methylpropyl)-4-(dimethylamino)-4-phenylcyclohexanol

Product 1

HCID 68920097(S)-N,N,3-trimethyl-4'-phenyl-2,3,4,9-tetrahydrospiro[carbazole-1,1'-cyclohexane]-4'-amine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (R)-1-(3-(1H-indol-3-yl)-2-methylpropyl)-4-(dimethylamino)-4-phenylcyclohexanol (100 mg, 0.25 mmol) in anhydrous 1,2-dichloroethane (10 mL) was mixed with trifluoromethane sulphonic acid trimethylsilyl ester (222 mg, 181 μL, 1 mmol) and stirred for 4 h at 50° C. After adding dichloromethane (10 mL) the solution was washed with 1 M potassium carbonate solution (2×10 mL), water (10 mL) and saturated sodium chloride solution (10 mL), dried with sodium sulphate and concentrated to low volume in a vacuum. The residue (90 mg) was taken up in methanol (10 mL) and stirred for 16 h at room temperature. The precipitated solid was separated from the solution by decanting, the remaining solid once again mixed with methanol, stirred and decanted, as a result of which Example No. 15 was obtained.

Workup

  1. washwas washed with 1 M potassium carbonate solution (2×10 mL), water (10 mL) and saturated sodium chloride solution (10 mL)
  2. dry with materialdried with sodium sulphate
  3. concentrationconcentrated to low volume in a vacuum
  4. stirringstirred for 16 h at room temperature
  5. customThe precipitated solid was separated from the solution
  6. customby decanting
  7. additionthe remaining solid once again mixed with methanol
  8. stirringstirred
  9. customdecanted
  10. custom15 was obtained

Sources & evidence

ORD record
ord-b9403343ce9f4f90aaf91d4b9b77ae10
Source dataset
uspto-grants-2012_10
Patent number
US08288430B2

Reaction notes

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