Tryptophol → HCID 44237779, compound

HRID 2066961Notes

Reaction equation

HRID 2066961 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][CH:6]1[CH2:11][C:10]([N:18]([CH3:20])[CH3:19])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][CH2:8][C:7]1=[O:21].[CH:25]1[CH:26]=[CH:27][C:28]2[NH:33][CH:32]=[C:31]([CH2:34][CH2:35]O)[C:29]=2[CH:30]=1.C[Si](OS(C(F)(F)F)(=O)=O)(C)C>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][CH:6]1[C:7]2([C:32]3[NH:33][C:28]4[C:29]([C:31]=3[CH2:34][CH2:35][O:21]2)=[CH:30][CH:25]=[CH:26][CH:27]=4)[CH2:8][CH2:9][C:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)([N:18]([CH3:19])[CH3:20])[CH2:11]1

Participants

5

Reactant 3

HCID 10685TryptopholHCID 65367Trimethylsilyl triflateHCID 67407146HCID 67407146, compound

Product 1

HCID 44237779HCID 44237779, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(±)-2-(3-fluorobenzyl)-4-dimethylamino-4-phenylcyclohexanone (325 mg, 1 mmol) together with tryptophol (161 mg, 1 mmol) was dissolved in dichloromethane (30 ml) and mixed with trifluoromethane sulphonic acid trimethylsilyl ester (0.22 ml, 1.14 mmol). The batch was stirred at RT for 2.5 h. A precipitate began to separate out after some time (approx. 1 h). For work up the reaction mixture was mixed with 2N NaOH (20 ml) and stirred for 20 min. During this the precipitate went into solution. The organic phase was separated and the aqueous phase extracted with dichloromethane (4×20 ml). The combined organic phases were dried with MgSO4. The solvent was then concentrated by evaporation in a vacuum. One of the possible diastereoisomers was isolated from the residue obtained (352 mg) by means of chromatographic purification [silica gel 60 G (10 g); ethyl acetate 150 ml].

Workup

  1. customto separate out after some time (approx. 1 h)
  2. additionFor work up the reaction mixture was mixed with 2N NaOH (20 ml)
  3. stirringstirred for 20 min
  4. customThe organic phase was separated
  5. extractionthe aqueous phase extracted with dichloromethane (4×20 ml)
  6. dry with materialThe combined organic phases were dried with MgSO4
  7. concentrationThe solvent was then concentrated by evaporation in a vacuum
  8. customOne of the possible diastereoisomers was isolated from the residue
  9. customobtained (352 mg)
  10. customby means of chromatographic purification [silica gel 60 G (10 g); ethyl acetate 150 ml]

Sources & evidence

ORD record
ord-b70e43d0efda42729a4500999e55bcf7
Source dataset
uspto-grants-2012_10
Patent number
US08293758B2

Reaction notes

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