Water → HCID 53683528, compound

HRID 264409Notes

Reaction equation

HRID 264409 reaction equation
O=[CH:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][CH:10]=2)[C:5]1=O.O.[NH2:21][CH2:22][C@H:23]([OH:25])[CH3:24]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:13]1([C:8]2[CH:7]=[C:6]3[C:11]([CH2:12][C:4]4[CH:3]=[CH:2][N:21]([CH2:22][C@H:23]([OH:25])[CH3:24])[C:5]=43)=[CH:10][CH:9]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 962WaterHCID 439938(2R)-1-aminopropan-2-olHCID 19036515HCID 19036515, compound

Product 1

HCID 53683528HCID 53683528, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent2×

Procedure

A solution of 2.5 g of (RS)-2-(2-oxoethyl)-6-phenyl-1-indanone and 80 mg of p-toluenesulfonic acid in 70 ml of anhydrous toluene was heated on a water separator. A solution of 3.0 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 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 7:3). 1.5 g (52%) of (R)-1-(7-phenyl-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 7:3)

Sources & evidence

ORD record
ord-88c5d6f2cf6247209bd7a56c3db5c002
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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