Water → (S)-tert-butyl 2-(t-butyldimethylsilyloxymethyl)aziridine-1-carboxylate

Temperature

0 °C

Ph3P (19.65 g, 75 mmol) was dissolved in 9:1 THF/CH3CN (600 mL) and cooled to 0° C., DIAD (14.7 mL, 75 mmol) was added dropwise over 15 min. After stirring for 30 min, a solution of (S)-2-(t-butoxycarbonylamino)-3-(t-butyldimethylsilyloxy)propan-1-ol (15.25 g, 50 mmol) in THF (100 mL) was added dropwise over 15 min, the reaction mixture was allowed to rt and stirred for 24 h. Water (100 mL) was added and volatiles were evaporated. The residue was partitioned between water (100 mL) and EtOAc (2×100 mL). The organic layers were washed with brine, dried over MgSO4 and evaporated. The residue was purified by silica chromatography to provide (S)-tert-butyl 2-(t-butyldimethylsilyloxymethyl)aziridine-1-carboxylate (7.8 g, 54%) as an oil. 1H NMR (CDCl3, 400 MHz): δ 0.07 (s, 6 H), 0.89 (s, 9 H), 1.45 (s, 9 H), 2.06 (d, J=3.6 Hz 1 H), 2.26 (d, J=6 Hz 1 H), 2.55 (m, 1 H), 3.64 (dd, J=16.4, 4.8 Hz, 1 H), 3.82 (dd, J=16.4, 4.4 Hz, 1 H).

1. customwas allowed to rt
2. stirringstirred for 24 h
3. customvolatiles were evaporated
4. customThe residue was partitioned between water (100 mL) and EtOAc (2×100 mL)
5. washThe organic layers were washed with brine
6. dry with materialdried over MgSO4
7. customevaporated
8. customThe residue was purified by silica chromatography

ORD record

ord-066d8ceda0d84528aca1a4f1bc5192e0

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455521B2