Boron tribromide → 2-(4-Benzyl-4-(dimethylamino)cyclohexyl)-3-methyl-1H-indol-5-ol

HRID 1095597Notes

Reaction equation

HRID 1095597 reaction equation
B(Br)(Br)Br.[CH2:5]([C:12]1([N:30]([CH3:32])[CH3:31])[CH2:17][CH2:16][CH:15]([C:18]2[NH:19][C:20]3[C:25]([C:26]=2[CH3:27])=[CH:24][C:23]([O:28]C)=[CH:22][CH:21]=3)[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(Cl)Cl>[CH2:5]([C:12]1([N:30]([CH3:32])[CH3:31])[CH2:13][CH2:14][CH:15]([C:18]2[NH:19][C:20]3[C:25]([C:26]=2[CH3:27])=[CH:24][C:23]([OH:28])=[CH:22][CH:21]=3)[CH2:16][CH2:17]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 667829431-Benzyl-4-(5-methoxy-3-methyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine

Product 1

HCID 249526002-(4-Benzyl-4-(dimethylamino)cyclohexyl)-3-methyl-1H-indol-5-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1 M solution of BBr3 in methylene chloride (3.48 ml, 3.48 mmol) was added to a solution of 1-benzyl-4-(5-methoxy-3-methyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine (less polar diastereoisomer, 437 mg, 1.16 mmol) in dry methylene chloride (50 ml) at RT, while stirring and with exclusion of moisture. After 10 min a precipitate precipitated out. The mixture was stirred at RT for 24 h.—For working up, sat. NaHCO3 solution (20 ml) was added to the mixture and the mixture was stirred for 48 h. The organic phase was separated off and the aqueous phase was extracted with methylene chloride (3×10 ml). The combined organic phases were dried over Na2SO4 and then concentrated. 2-(4-Benzyl-4-(dimethylamino)cyclohexyl)-3-methyl-1H-indol-5-ol (less polar diastereoisomer) was obtained in this way in a yield of 291 mg (69%).

Workup

  1. customAfter 10 min a precipitate precipitated out
  2. stirringThe mixture was stirred at RT for 24 h.—
  3. additionsat. NaHCO3 solution (20 ml) was added to the mixture
  4. stirringthe mixture was stirred for 48 h
  5. customThe organic phase was separated off
  6. extractionthe aqueous phase was extracted with methylene chloride (3×10 ml)
  7. dry with materialThe combined organic phases were dried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e27eca00901048e2920576c644deffd1
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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