1-Amino-2-propanol → (RS)-1-(8-methoxy-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol

HRID 264562Notes

Reaction equation

HRID 264562 reaction equation
O=[CH:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[C:7]([O:13][CH3:14])[CH:8]=[CH:9][CH:10]=2)[C:5]1=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.[NH2:28][CH2:29][CH:30]([OH:32])[CH3:31]>C1(C)C=CC=CC=1>[CH3:14][O:13][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[C:5]1[N:28]([CH2:29][CH:30]([OH:32])[CH3:31])[CH:2]=[CH:3][C:4]=1[CH2:12]2

Participants

6

Reactant 4

HCID 41-Amino-2-propanolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 10512377(RS)-2-(2-oxoethyl)-7-methoxy-1-indanone

Product 1

HCID 10657863(RS)-1-(8-methoxy-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-olYield 45.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 2.04 g of (RS)-2-(2-oxoethyl)-7-methoxy-1-indanone and 80 mg of p-toluenesulfonic acid in 90 ml of anhydrous toluene was heated on a water separator. A solution of 3.0 g of (RS)-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 35 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 2:3). There was obtained 1.1 g (45%) of (RS)-1-(8-methoxy-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol 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 2:3)

Sources & evidence

ORD record
ord-85bb2ecb68274bb49f1ca97aedc3fb95
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

Loading…