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

HRID 264367

Reaction equation

HRID 264367 reaction equation
O=[CH:2][CH2:3][CH:4]1[C:12]([CH3:14])([CH3:13])[C:11]2[C:6](=[CH:7][C:8]([O:15][CH3:16])=[CH:9][CH:10]=2)[C:5]1=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.[NH2:30][CH2:31][C@H:32]([OH:34])[CH3:33]>C1(C)C=CC=CC=1>[CH3:16][O:15][C:8]1[CH:7]=[C:6]2[C:11]([C:12]([CH3:14])([CH3:13])[C:4]3[CH:3]=[CH:2][N:30]([CH2:31][C@H:32]([OH:34])[CH3:33])[C:5]=32)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 439938(2R)-1-aminopropan-2-olHCID 10513740(RS)-2-(2-oxoethyl)-6-methoxy-3,3-dimethyl-1-indanone

Product 1

HCID 54520992(R)-1-(7-methoxy-4,4-dimethyl-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-olYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 4.94 g of (RS)-2-(2-oxoethyl)-6-methoxy-3,3-dimethyl-1-indanone and 220 ml of p-toluenesulfonic acid in 200 ml of anhydrous toluene was heated on a water separator. A solution of 6.39 g of (R)-1-amino-2-propanol in 40 ml of anhydrous toluene was added dropwise to the boiling solution over a period of 5 minutes, during which the solvent was reduced to a volume of 40 ml. The cooled reaction mixture was purified by column chromatography on silica gel (diethyl ether/hexane 7:3). 3.42 g (60%) of (R)-1-(7-methoxy-4,4-dimethyl-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-69ea06dddbad4f3d9374d06dbb6d8137
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Linked notes

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