1-Amino-2-propanol → (RS)-1-(1,4-dihydro-[1]benzothiopyrano[4,3-b]pyrrol-1-yl)-propan-2-ol

HRID 264554Notes

Reaction equation

HRID 264554 reaction equation
O=CC[CH:4]1[CH2:13][C:12](=O)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[S:5]1.O.[NH2:16][CH2:17][CH:18]([OH:20])[CH3:19].[C:21]1(C)C=CC=C[CH:22]=1>C1(C)C=CC(S(O)(=O)=O)=CC=1>[N:16]1([CH2:17][CH:18]([OH:20])[CH3:19])[CH:22]=[CH:21][C:13]2[CH2:4][S:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:12]1=2

Participants

6

Reactant 4

HCID 41-Amino-2-propanolHCID 962WaterHCID 1140Toluene2×HCID 190364592-(2-Oxoethyl)-4-thiochromanone

Product 1

HCID 19036598(RS)-1-(1,4-dihydro-[1]benzothiopyrano[4,3-b]pyrrol-1-yl)-propan-2-olYield 76%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

A solution of 2 g of 2-(2-oxoethyl)-4-thiochromanone and 120 mg of p-toluenesulfonic acid in 100 ml of anhydrous toluene was heated on a water separator, A solution of 2.9 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 35 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/toluene 1:1). There were obtained 1.8 g (76%) of (RS)-1-(1,4-dihydro-[1]benzothiopyrano[4,3-b]pyrrol-1-yl)-propan-2-ol as a pale brown solid which was used in the next reaction without further recrystallization.

Workup

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

Sources & evidence

ORD record
ord-28b6cf101b0e4ae5a5c483314ca85db1
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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