1-Amino-2-propanol → HCID 19036610, compound

HRID 264504Notes

Reaction equation

HRID 264504 reaction equation
O=[CH:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([O:13][CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:9][CH:10]=2)[C:5]1=O.O.[NH2:21][CH2:22][CH:23]([OH:25])[CH3:24]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH:14]1([O:13][C:8]2[CH:7]=[C:6]3[C:11]([CH2:12][C:4]4[CH:3]=[CH:2][N:21]([CH2:22][CH:23]([OH:25])[CH3:24])[C:5]=43)=[CH:10][CH:9]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 41-Amino-2-propanolHCID 962WaterHCID 19036568HCID 19036568, compound

Product 1

HCID 19036610HCID 19036610, compoundYield 48.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent2×

Procedure

A solution of 2.58 g of (RS)-2-(2-oxoethyl)-6-cyclopentoxy-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 (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 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). 1.44 g (48%) of (RS)-1-(7-cyclopentoxy-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol were obtained as a light yellow 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-a98bf87aaf824379b39788ff515be5ef
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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