tert-Butyldimethylsilyl chloride → 3-((tert-Butyldimethylsilanyl)oxy)azetidine

A solution of tert-butylchlorodimethylsilane (12.01 g, 79.69 mmol) in DCM (20 mL) was added dropwise to a stirred 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).

1. concentrationThe reaction mixture was concentrated
2. additiondiluted with EtOAc (75 mL)
3. washwashed sequentially with saturated NaHCO3 (25 mL), water (20 mL), and saturated brine (20 mL)
4. dry with materialThe organic layer was dried (MgSO4)
5. filtrationfiltered
6. customevaporated

ORD record

ord-c1a2b3759e274760aefc60c382349073

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143263B2