Diethyl Ether → HCID 19036449, compound

A 2M phenyllithium solution was added dropwise over 5 minutes to a solution, cooled to 0°, of 3.55 g of (RS)-1-(2-azido-propyl)-7-mesyloxycarbonyl-1,4-dihydro-indeno[1,2-b]pyrrole, 90 ml of anhydrous diethyl ether and 90 ml of anhydrous tetrahydrofuran. After 15 minutes at this temperature, an additional 5.87 ml of the phenyllithium solution were added dropwise and the mixture was stirred for an additional 5 minutes. Subsequently, the reaction mixture was treated with 50 ml of a saturated ammonium chloride solution and 25 ml of water. The mixture was extracted once with 50 ml of ethyl acetate and the aqueous phase was made slightly acidic with 1N hydrochloric acid and extracted three times with 100 ml of ethyl acetate each time. The combined organic phases were washed once with 100 ml of saturated sodium chloride solution, dried over magnesium sulfate and concentrated in a vacuum. 2.7 g (99%) of (RS)-1-(2-azido-propyl)-7-hydroxy-1,4-dihydro-indeno[1,2-b]pyrrole were obtained as a brown oil.

1. extractionThe mixture was extracted once with 50 ml of ethyl acetate
2. extractionextracted three times with 100 ml of ethyl acetate each time
3. washThe combined organic phases were washed once with 100 ml of saturated sodium chloride solution
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated in a vacuum

ORD record

ord-aea65028a985468e97284f4967c4f025

Source dataset

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05646173