Reaktion #1523990

Reaktionsgleichung

lithium hydroxide monohydrate

methyl (3S)-3-[(tert-butoxycarbonyl)amino]-1-(1-hydroxy-1-methylethyl)cyclopentanecarboxylate

methanol

water

→

desired product

Ausbeute 49.6%

(3S)-3-[(tert-Butoxycarbonyl)amino]-1-(1-hydroxy-1-methylethyl)cyclopentanecarboxylic acid

Ausbeute 49.6%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe organic solvents were evaporated
2. 2
   Waschenthe aqueous layer was washed with ether one time
3. 3
   Extraktionextracted with methylene chloride three times
4. 4
   SonstigeThe combined extracts were dried
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated

Vorschrift

To a solution of methyl (3S)-3-[(tert-butoxycarbonyl)amino]-1-(1-hydroxy-1-methylethyl)cyclopentanecarboxylate (1.0 g, 3.3 mmol) in a mixture of THF (30 mL), methanol (30 mL) and water (6 mL) was added lithium hydroxide monohydrate (0.22 g, 5.3 mmol) and the mixture refluxed overnight (110 ° C). The organic solvents were evaporated and the aqueous layer was washed with ether one time. The aqueous layer was then acidified with 6 N HCl to about pH 4 and extracted with methylene chloride three times. The combined extracts were dried, filtered, and concentrated to provide the desired product (0.47 g, 49%).

Quelle