Reacción #41288

Ecuación de reacción

tert-butyl[(1S)-2-(3-methoxyphenyl)-1-methyl-2-oxoethyl]carbamate

aluminium isopropoxide

2-propanol

→

subtitle compound

Rendimiento 98.5%

tert-Butyl[(1S,2R)-2-hydroxy-2-(3-methoxyphenyl)-1-methylethyl]carbamate

Rendimiento 98.5%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was partitioned between ethyl acetate (200 mL) and hydrochloric acid (1M, 200 mL)
2. 2
   LavadoThe organic phase was washed with water (200 mL)
3. 3
   Secadodried over magnesium sulfate
4. 4
   Concentraciónconcentrated

Procedimiento

A mixture of tert-butyl[(1S)-2-(3-methoxyphenyl)-1-methyl-2-oxoethyl]carbamate (13.6 g, 48.7 mmol), aluminium isopropoxide (1.99 g, 9.70 mmol), 2-propanol (41 mL, 535 mmol) in toluene (63 mL) was stirred under an atmosphere of argon at 50° C. overnight. LC/MS showed complete conversion into the alcohol. The mixture was partitioned between ethyl acetate (200 mL) and hydrochloric acid (1M, 200 mL). The organic phase was washed with water (200 mL), dried over magnesium sulfate and concentrated to give the subtitle compound as a syrup (13.5 g). The compound was used in the next step without further purification.

Fuente