Reacción #10488

Ecuación de reacción

2-(S)-Methanesulfonyloxymethyl-azetidine-1-carboxylic acid tert-butyl ester

lithium triethylborohydride

ethyl acetate

→

title compound

Rendimiento 30.0%

2-(R)-Methyl-azetidine-1-carboxylic acid tert-butyl ester

Rendimiento 30.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with water
2. 2
   Lavadowashed with 0.25 M HCl
3. 3
   Lavadowashed with NaHCO3 solution
4. 4
   Lavadowashed with brine (2×)
5. 5
   Secadodried (MgSO4)
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated
8. 8
   Otropurified by chromatography on silica gel eluting with a gradient of 10:1

Procedimiento

2-(S)-Methanesulfonyloxymethyl-azetidine-1-carboxylic acid tert-butyl ester was (4.83 g, 18.2 mmol) was taken up in THF (11 mL), cooled to 0° C. under N2, treated drop-wise with a lithium triethylborohydride (1.0 M in THF, 73 mL), stirred at ambient temperature for 6 hours, treated with ethyl acetate (500 mL), washed with water, washed with 0.25 M HCl, washed with NaHCO3 solution, washed with brine (2×), dried (MgSO4), filtered, concentrated and purified by chromatography on silica gel eluting with a gradient of 10:1 and then 5:1 hexane:ethyl acetate to provide 0.95 g (30%) of the title compound. 1H NMR (300 MHz, CDCl3) δ 1.37 (d, J=6.10 Hz, 3 H) 1.44 (s, 9 H) 1.76 (m, 1 H) 2.27 (m, 1 H) 3.81 (t, J=7.46 Hz, 2 H) 4.28 (m, 1 H).

Fuente