Reacción #66336

Ecuación de reacción

N-Boc-1(R)-amino-2(S)-hydroxy-cyclopentane-4(S)-carboxylic acid methyl ester

imidazole

TBSCl

HCl

→

desired acid

Rendimiento 87.1%

N-Boc-1(R)-amino-2(S)-tert-butyldimethylsilyloxy-cyclopentane-4(S) -carboxylic acid

Rendimiento 87.1%

Disolventes

DCM

isopropanol

chloroform

NaOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaby heating at 40° C. for 1 hour
2. 2
   TemperaturaThe reaction mixture was cooled to room temperature
3. 3
   Otrowas quenched with H2O (3 mL)
4. 4
   OtroThe organic layer was separated
5. 5
   Concentraciónwas concentrated to dryness
6. 6
   Otroto yield a residue, which
7. 7
   TemperaturaThe reaction was cooled to 0° C.
8. 8
   Otrothe organic layer was separated
9. 9
   Secadodried over Na2SO4
10. 10
    Concentraciónconcentrated to dryness

Procedimiento

To a stirring solution of N-Boc-1(R)-amino-2(S)-hydroxy-cyclopentane-4(S)-carboxylic acid methyl ester (0.622 g, 2.40 mmol) in DCM (1.9 mL) was added imidazole (0.164 g, 2.41 mmol), DMAP (0.047 g, 0.35 mmol) and TBSCl (0.363 g, 2.40 mmol) and the reaction was stirred at room temperature for 18 hours, followed by heating at 40° C. for 1 hour. The reaction mixture was cooled to room temperature, and was quenched with H2O (3 mL). The organic layer was separated and was concentrated to dryness to yield a residue, which was dissolved in isopropanol (6 mL) and 1M NaOH (2.9 mL), and the reaction was heated at 60° C. for 1 hour. The reaction was cooled to 0° C. and slowly acidified to pH 3 with 1M HCl (3 mL). After adding chloroform (18 mL), the organic layer was separated, dried over Na2SO4, and concentrated to dryness to yield the desired acid (0.75 g, 2.09 mmol, 87.1% yield).

Fuente