Hydrochloric Acid → 2-Cyclopentene-1-methanol, 4-amino-, hydrochloride (1:1), (1S,4R)-

87.8 g of (1R, 4 S)-1-BOC-amino-4-hydroxymethyl-2-cyclopentene were dissolved in 270 ml of 2 N HCl and 1340 ml of methanol. The mixture was boiled under reflux for 4.5 h. After distillation of the methanol, the residue was dissolved in 800 ml of water. The aqueous solution was extracted twice with 340 ml of ethyl acetate. The aqueous phase was completely evaporated (50° C./60 mbar). The solid was dried at 50° C. in vacuo, suspended in 150 ml of diethyl ether, filtered off and washed twice with 50 ml of diethyl ether. Drying resulted in the title compound in a yield of 95% (58.4 g).

1. temperatureunder reflux for 4.5 h
2. distillationAfter distillation of the methanol
3. dissolutionthe residue was dissolved in 800 ml of water
4. extractionThe aqueous solution was extracted twice with 340 ml of ethyl acetate
5. customThe aqueous phase was completely evaporated (50° C./60 mbar)
6. customThe solid was dried at 50° C. in vacuo
7. filtrationfiltered off
8. washwashed twice with 50 ml of diethyl ether
9. customDrying

ORD record

ord-4ab355fbd46a47598f6d8e9e9fe7f710

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06252112B1