Reacción #164153

Ecuación de reacción

(S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid

DCC

HOBt

3(R)-quinuclidinol

→

(S)-((R)-quinuclidin-3-yl) 2-(tert-butoxycarbonylamino)-3-phenylpropanoate

Rendimiento 80.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent is evaporated
2. 2
   Otrothe residue is partitioned between EtOAc (100 mL) and 2M K2CO3 (50 mL)
3. 3
   Otrothe organic layer is separated
4. 4
   Lavadowashed with brine
5. 5
   Secadodried over Na2SO4
6. 6
   OtroThe resulting crude is purified by flash chromatography (DCM/MeOH=95/5, 0.1% NH3 (aq.))
7. 7
   Otroto obtain 1.12 g of I19 (80% yield)

Procedimiento

To a solution of (S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid (1.03 g, 3.81 mmol) in THF (70 mL), are added DCC (1.03 g, 4.91 mmol), HOBt (660 mg, 4.90 mmol) and 3(R)-quinuclidinol (1.18 g, 9.48 mmol) and the resulting mixture is stirred for 12 hours at RT under nitrogen flowstream (LC-MS monitoring: complete conversion). The solvent is evaporated and the residue is partitioned between EtOAc (100 mL) and 2M K2CO3 (50 mL); the organic layer is separated, washed with brine and dried over Na2SO4. The resulting crude is purified by flash chromatography (DCM/MeOH=95/5, 0.1% NH3 (aq.)) to obtain 1.12 g of I19 (80% yield).

Fuente