(S)-(1-TRITYLAZIRIDIN-2-YL)METHANOL synthesis

Yield:152706-23-5 99%

Reaction Conditions:

with methanol;lithium borohydride in tetrahydrofuran at 0 - 20; for 22 h;

Steps:

6 Synthesis of (S)-N-triphenylmethyl-aziridinylmethanol 11

To a solution of methyl (S)-N-triphenylmethyl aziridinate 1 (0.858 g, 2.5 mmol) in THF (25 mL) was added LiBH₄ (0.202 g, 9.2 mmol) at 0 °C. Methanol (6 mL) was added then dropwise over a period of 6 h and the mixture was stirred for 16 h at room temperature.
After completion of the reaction, water was added, and it was extracted with AcOEt.
The combined organic fractions were dried over MgSO₄, and the solvent was evaporated under vacuum to afford 11 in 99% yield (0.781 g) as colorless crystals, mp 118-120 °C; [α]_D = +7.1 (c 1, CHCl₃); ¹H NMR (CDCl₃): δ = 1.05 (d, J = 6.0 Hz, 1H), 1.49-1.51 (m, 1H), 1.79 (d, J = 3 Hz, 1H), 2.10 (dd, J = 4.2 Hz, 7.8 Hz, OH), 3.61-3.64 (m, 1H), 3.79-3.82 (m, 1H), 7.14-7.40 (m, 15H); ¹³C NMR (CDCl₃): δ = 23.8 (CH₂), 33.2 (CH), 61.6 (CH₂), 73.8 (C_q), 126.9 (C_ar), 127.6 (C_ar), 129.4 (C_ar), 144.3 (C_{q ar}).
Other spectroscopic data are in agreement with the literature.
³⁶

References:

Jarzyski, Szymon;Lesniak, Stanislaw;Pieczonka, Adam M.;Rachwalski, Michal [Tetrahedron Asymmetry,2015,vol. 26,# 1,p. 35 - 40]