Water → (R)-1-(7-bromo-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol

HRID 264398Notes

Reaction equation

HRID 264398 reaction equation
O=[CH:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([Br:13])=[CH:9][CH:10]=2)[C:5]1=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.[NH2:27][CH2:28][C@H:29]([OH:31])[CH3:30]>C1(C)C=CC=CC=1>[Br:13][C:8]1[CH:7]=[C:6]2[C:11]([CH2:12][C:4]3[CH:3]=[CH:2][N:27]([CH2:28][C@H:29]([OH:31])[CH3:30])[C:5]=32)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 439938(2R)-1-aminopropan-2-olHCID 10610858(RS)-2-(2-oxoethyl)-6-bromo-1-indanone

Product 1

HCID 53850920(R)-1-(7-bromo-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-olYield 52%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 2.0 g of (RS)-2-(2-oxoethyl)-6-bromo-1-indanone and 80 mg of p-toluenesulfonic acid in 90 ml of anhydrous toluene was heated on a water separator. A solution of 2.37 g of (R)-1-amino-2-propanol in 10 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 45 minutes, during which the solvent was reduced to a volume of 20 ml. The cooled reaction mixture was purified by column chromatography on silica gel (diethyl ether/hexane 4:1). 1.19 g (52%) of (R)-1-(7-bromo-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol were obtained as a brown oil.

Workup

  1. customThe cooled reaction mixture
  2. customwas purified by column chromatography on silica gel (diethyl ether/hexane 4:1)

Sources & evidence

ORD record
ord-a49279789ab8482ba14a90abb24321c7
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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