Trifluoroacetic acid → 4-(4-{2-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethylamino}cyclohexyl)phenol

HRID 1292403Notes

Reaction equation

HRID 1292403 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][NH2:20])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[OH:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]2[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]2)=[CH:24][CH:23]=1.FC(F)(F)C(O)=O.C([BH3-])#N.[Na+]>CO>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][NH:20][CH:31]2[CH2:30][CH2:29][CH:28]([C:25]4[CH:26]=[CH:27][C:22]([OH:21])=[CH:23][CH:24]=4)[CH2:33][CH2:32]2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 45989164-(4'-Hydroxyphenyl)cyclohexanoneHCID 5003444Sodium cyanoborohydrideHCID 221009192-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethylamine

Product 1

HCID 189142434-(4-{2-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethylamino}cyclohexyl)phenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 2-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethylamine (EXAMPLE 2, Step D, 345 mg) and 4-(4-hydroxyphenyl)cyclohexanone (62 mg) were solvated in 8 mL dry methanol to which ca. 2 g powdered 3 Å molecular sieves were added. The pH of this mixture was adjusted to 6 by the addition of 0.65 mL of a 10% solution of trifluoroacetic acid in methanol and then 90 mg sodium cyanoborohydride was added and the mixture stirred at room temperature. After 20 hours, the mixture was filtered through diatomaceous earth, concentrated in vacuo and purified by flash chromatography on silica gel [(methylene chloride:methanol:, 92:8) then again (chloroform:methanol, 90:10) to separate the diastereomers] to give the title compound (isomer A 40 mg, isomer B 36 mg). m/e=439 (M+H)

Workup

  1. additionwere added
  2. filtrationthe mixture was filtered through diatomaceous earth
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography on silica gel [(methylene chloride:methanol:, 92:8)
  5. customagain (chloroform:methanol, 90:10) to separate the diastereomers]

Sources & evidence

ORD record
ord-d548b321bd104466a4c96bb178bd34b6
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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