1-Amino-2-propanol → HCID 19036564, compound

HRID 264509Notes

Reaction equation

HRID 264509 reaction equation
O=[CH:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:9][CH:10]=2)[C:5]1=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.[NH2:31][CH2:32][CH:33]([OH:35])[CH3:34]>C1(C)C=CC=CC=1>[S:14]([O:13][C:8]1[CH:7]=[C:6]2[C:11]([CH2:12][C:4]3[CH:3]=[CH:2][N:31]([CH2:32][CH:33]([OH:35])[CH3:34])[C:5]=32)=[CH:10][CH:9]=1)([CH3:17])(=[O:16])=[O:15]

Participants

6

Reactant 4

HCID 41-Amino-2-propanolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 19036518HCID 19036518, compound

Product 1

HCID 19036564HCID 19036564, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 2.31 g of (RS)-2-(2-oxoethyl)-6-mesyloxy-1-indanone and 110 mg of p-toluenesulfonic acid in 70 ml of anhydrous toluene was heated on a water separator. A solution of 2.58 g of (RS)-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 time 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 2:3). 0.74 g (28%) of (RS)-1-(7-mesyloxy-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol was obtained as a light brown solid which was used directly in the next reaction.

Workup

  1. customThe cooled reaction mixture
  2. customwas purified by column chromatography on silica gel (ethyl acetate/hexane 2:3)

Sources & evidence

ORD record
ord-078c0fc79883408795c807551f4d5609
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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