Water → HCID 53760578, compound

HRID 264446Notes

Reaction equation

HRID 264446 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:16][CH3:17])=[C:9]([Cl:15])[CH:10]=2)[C:5]1=O.O.[NH2:20][CH2:21][C@H:22]([OH:24])[CH3:23]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:15][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:16][CH3:17])[C:5]1[N:20]([CH2:21][C@H:22]([OH:24])[CH3:23])[CH:2]=[CH:3][C:4]=1[C:12]2([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 962WaterHCID 439938(2R)-1-aminopropan-2-olHCID 19036502HCID 19036502, compound

Product 1

HCID 53760578HCID 53760578, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent2×

Procedure

A solution of 6.67 g of (RS)-2-(2-oxoethyl)-5-chloro-6-methoxy-3,3-dimethyl-1-indanone and 150 mg of p-toluenesulfonic acid in 200 ml of anhydrous toluene was heated on a water separator. A solution of 7.51 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. Subsequently, the mixture was boiled for an additional 45 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 (ethyl acetate/hexane 1:1). 7.0 g (92%) of (R)-1-(6-chloro-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 (ethyl acetate/hexane 1:1)

Sources & evidence

ORD record
ord-3517c730454f4dc3aa6d93e5fd97e974
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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