Skatole → HCID 44513835, compound

HRID 1011633Notes

Reaction equation

HRID 1011633 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[CH3:11][N:12]([CH3:34])[C:13]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:18][CH2:17][C:16]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)(O)[CH2:15][CH2:14]1.C[Si](OS(C(F)(F)F)(=O)=O)(C)C.[OH-].[Na+]>ClCCl.O=O>[CH3:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([C:16]2([C:3]3[NH:4][C:5]4[C:10]([C:2]=3[CH3:1])=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH2:17][CH2:18][C:13]([N:12]([CH3:11])[CH3:34])([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:14][CH2:15]2)=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 6736SkatoleHCID 14798Sodium HydroxideHCID 65367Trimethylsilyl triflateHCID 66911352HCID 66911352, compound

Product 1

HCID 44513835HCID 44513835, compound

Reagents, catalysts & solvents 2

HCID 977OxygenSolventHCID 6344DichloromethaneSolvent

Procedure

3-methyl-1H-indol (393 mg, 3 mmol) and the more non-polar 4-dimethylamino-1-(4-methoxyphenyl)-4-phenylcyclohexanol (651 mg, 2 mmol) were dissolved in absolute dichloromethane (50 ml) with the exclusion of oxygen, mixed with trifluoromethane sulphonic acid trimethylsilyl ester (581 μl, 3 mmol) and stirred for 16 h at room temperature. For work up the batch was mixed with 5N NaOH (50 ml) and stirred for 1 h at room temperature. The aqueous phase was separated and extracted with dichloromethane (3×25 ml). The combined organic phases were dried over Na2SO4 and then concentrated to low volume. A raw product was isolated that was separated by chromatography [silica gel 60 (50 g); ethyl acetate (1000 ml)]. The product was obtained as a white solid with a yield of 600 mg (68%) and a melting point of 90-95° C. This concerned a mixture of two diastereoisomers (approx. 1:1), which could not be separated because of the identical Rt value.

Workup

  1. stirringstirred for 1 h at room temperature
  2. customThe aqueous phase was separated
  3. extractionextracted with dichloromethane (3×25 ml)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated to low volume

Sources & evidence

ORD record
ord-5696049821d74b13b56bb090dda4e32f
Source dataset
uspto-grants-2011_07
Patent number
US07977370B2

Reaction notes

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