Skatole → HCID 44514151, compound

HRID 1011635Notes

Reaction equation

HRID 1011635 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.[O:11]1[C:15]2[CH:16]=[CH:17][C:18]([C:20]3(O)[CH2:25][CH2:24][C:23]([N:32]([CH3:34])[CH3:33])([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:22][CH2:21]3)=[CH:19][C:14]=2[O:13][CH2:12]1.C[Si](OS(C(F)(F)F)(=O)=O)(C)C.[OH-].[Na+]>ClCCl.O=O>[O:11]1[C:15]2[CH:16]=[CH:17][C:18]([C:20]3([C:3]4[NH:4][C:5]5[C:10]([C:2]=4[CH3:1])=[CH:9][CH:8]=[CH:7][CH:6]=5)[CH2:21][CH2:22][C:23]([N:32]([CH3:34])[CH3:33])([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:24][CH2:25]3)=[CH:19][C:14]=2[O:13][CH2:12]1

Participants

7

Reactant 4

HCID 6736SkatoleHCID 14798Sodium HydroxideHCID 65367Trimethylsilyl triflateHCID 66911429HCID 66911429, compound

Product 1

HCID 44514151HCID 44514151, compound

Reagents, catalysts & solvents 2

HCID 977OxygenSolventHCID 6344DichloromethaneSolvent

Procedure

3-methyl-1H-indole (393 mg, 3 mmol) and the more polar 1-(benzo[d][1,3]dioxol-5-yl)-4-(dimethylamino)-4-phenylcyclohexanol (679 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 purified by chromatography [silica gel 60 (50 g); ethyl acetate (1000 ml)]. The product was obtained as a white solid with a yield of 545 mg (60%) and a melting point of 235-238° C. This concerned one of two possible diastereoisomers.

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-7662caac9b4c42d1846a8b7c8ff2937f
Source dataset
uspto-grants-2011_07
Patent number
US07977370B2

Reaction notes

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