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

HRID 1095596Notes

Reaction equation

HRID 1095596 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 (1.03 ml, 1.03 mmol) was added to a solution of 1-benzyl-4-(5-methoxy-3-methyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine (more polar diastereoisomer, 130 mg, 0.345 mmol) in dry methylene chloride (20 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 (15 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 (polar diastereomer) was obtained in this way in a yield of 63 mg (50%).

Workup

  1. customAfter 10 min a precipitate precipitated out
  2. stirringThe mixture was stirred at RT for 24 h.—
  3. additionsat. NaHCO3 solution (15 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-40744d5c1e9d40c8a60cd106c8d8536f
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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