Water → HCID 53839456, compound

HRID 264402Notes

Reaction equation

HRID 264402 reaction equation
O=[CH:2][CH2:3][CH:4]1[C:12]([CH2:15][CH3:16])([CH2:13][CH3:14])[C:11]2[C:6](=[CH:7][C:8]([O:17][CH3:18])=[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>[CH3:18][O:17][C:8]1[CH:7]=[C:6]2[C:11]([C:12]([CH2:15][CH3:16])([CH2:13][CH3:14])[C:4]3[CH:3]=[CH:2][N:21]([CH2:22][C@H:23]([OH:25])[CH3:24])[C:5]=32)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 439938(2R)-1-aminopropan-2-olHCID 19036488HCID 19036488, compound

Product 1

HCID 53839456HCID 53839456, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent2×

Procedure

A solution of 3.9 g of (RS)-2-(2-oxoethyl)-6-methoxy-3,3-diethyl-1-indanone and 120 mg of p-toluenesulfonic acid in 100 ml of anhydrous toluene was heated on a water separator. A solution of 4.5 g of (R)-1-amino-2-propanol in 30 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 (ethyl acetate/hexane 1:1). 2.73 g (61%) of (R)-1-(7-methoxy-4,4-diethyl-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol were obtained as a red-brown oil.

Workup

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

Sources & evidence

ORD record
ord-c3663b4068a544ab93dab9cb5f4056f2
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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