Water → (R)-1-(4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl)-propan-2-ol

HRID 264376Notes

Reaction equation

HRID 264376 reaction equation
O=[CH:2][CH2:3][CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[CH:9][CH:10]=2)[C:5]1=O.O.[NH2:18][CH2:19][C@H:20]([OH:22])[CH3:21]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:15][O:14][C:8]1[CH:9]=[CH:10][C:11]2[CH2:12][CH2:13][C:4]3[CH:3]=[CH:2][N:18]([CH2:19][C@H:20]([OH:22])[CH3:21])[C:5]=3[C:6]=2[CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 439938(2R)-1-aminopropan-2-olHCID 19036405(RS)-2-(2-oxoethyl)-7-methoxy-1-tetralone

Product 1

HCID 54152718(R)-1-(4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl)-propan-2-olYield 95.4%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent2×

Procedure

A solution of 2 g of (RS)-2-(2-oxoethyl)-7-methoxy-1-tetralone and 100 mg of p-toluenesulfonic acid in 90 ml of anhydrous toluene was heated on a water separator. A solution of 2.78 g of (R)-1-amino-2-propanol in 20 ml of anhydrous toluene was added dropwise to the boiling solution over a period of 5 minutes. Subsequently, the mixture was boiled for an additional 30 minutes, during which the solvent was reduced to a volume of 25 ml. The cooled reaction mixture was purified by column chromatography on silica gel (ethyl acetate/toluene 1:1). 2.25 g (94%) of (R)-1-(4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl)-propan-2-ol were obtained as a brown oil which was used directly in the next reaction.

Workup

  1. customThe cooled reaction mixture
  2. customwas purified by column chromatography on silica gel (ethyl acetate/toluene 1:1)

Sources & evidence

ORD record
ord-6edc7bbbfb6948558eca3d436fc13ee0
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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