Reacción #742294

Ecuación de reacción

N-ethyl-N-isopropylpropan-2-amine

tert-butylchlorodimethylsilane

azetidin-3-ol hydrochloride

→

product

Rendimiento 74.0%

Azetidin-3-yloxy-tert-butyl-dimethylsilane

Rendimiento 74.0%

Disolventes

DCM

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe reaction mixture was concentrated
2. 2
   workup.ADDITIONdiluted with EtOAc (75 mL)
3. 3
   Lavadowashed sequentially with saturated NaHCO3 (25 mL), water (20 mL), and saturated brine (20 mL)
4. 4
   SecadoThe organic layer was dried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated

Procedimiento

A solution of tert-butylchlorodimethylsilane (12.01 g, 79.69 mmol) in DCM (20 mL) was added dropwise to a stiffed solution of azetidin-3-ol hydrochloride (CAS no. 18621-18-6) (8.73 g, 79.69 mmol) and anhydrous N-ethyl-N-isopropylpropan-2-amine (34.1 mL, 199.22 mmol) in DCM (20 mL) cooled to 10° C., over a period of 2 minutes under nitrogen. The resulting solution was stirred at ambient temperature for 20 hours. The reaction mixture was concentrated, diluted with EtOAc (75 mL), and washed sequentially with saturated NaHCO3 (25 mL), water (20 mL), and saturated brine (20 mL). The organic layer was dried (MgSO4), filtered and evaporated to afford the product (11.1 g, 74%). 1H NMR (400 MHz, CDCl3) δ 0.04 (6H, s), 0.87 (9H, m), 2.80 (1H, s), 3.57-3.61 (2H, m), 3.67-3.71 (2H, m), 4.57-4.64 (1H, m).

Fuente