Reaction #742295

Reaction equation

tert-Butyldimethylsilyl chloride

1-benzhydrylazetidin-3-ol

imidazole

→

product

Yield 113.0%

(1-Benzhydrylazetidin-3-yl)oxy-tert-butyl-dimethylsilane

Yield 113.0%

Solvents

DCM

Conditions

Workup

1. 1
   Otherat r.t.
2. 2
   OtherThe reaction mixture was quenched with water
3. 3
   workup.ADDITIONpoured onto a phase separator
4. 4
   Otherevaporated

Procedure

tert-Butyldimethylsilyl chloride (1.524 g, 10.11 mmol) was added to 1-benzhydrylazetidin-3-ol (CAS no. 18621-17-5) (2.2 g, 9.19 mmol) and imidazole (1.565 g, 22.98 mmol) in DCM (46.0 mL) at r.t. under nitrogen. The resulting solution was stirred at r.t. for 3 hours. The reaction mixture was quenched with water, poured onto a phase separator and evaporated to afford the product (3.66 g, 113%). 1H NMR (400 MHz, CDCl3) δ 0.00 (6H, s), 0.85 (9H, s), 2.81 (2H, s), 3.52 (2H, s), 4.35 (1H, s), 4.40-4.49 (1H, m), 7.08-7.43 (10H, m); m/z (ES+) (M+H)+=354.55; HPLC tR=2.04 min.

Source