Reaction #742294

Reaction equation

N-ethyl-N-isopropylpropan-2-amine

tert-butylchlorodimethylsilane

azetidin-3-ol hydrochloride

→

product

Yield 74.0%

Azetidin-3-yloxy-tert-butyl-dimethylsilane

Yield 74.0%

Solvents

DCM

DCM

Conditions

Workup

1. 1
   ConcentrationThe reaction mixture was concentrated
2. 2
   workup.ADDITIONdiluted with EtOAc (75 mL)
3. 3
   Washwashed sequentially with saturated NaHCO3 (25 mL), water (20 mL), and saturated brine (20 mL)
4. 4
   DryingThe organic layer was dried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated

Procedure

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).

Source