Reacción #155403

Ecuación de reacción

N-Boc-3-methylene-cyclobutanamine

K2CO3

→

N-Boc-3-amino-cyclobutanone

Rendimiento 177.6%

Disolventes

DCM

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroDuring the course of the reaction
2. 2
   Filtraciónupon completion, the reaction mixture was filtered through a pad of celite
3. 3
   OtroThe filtrates were transferred to a separatory funnel
4. 4
   Extracciónthe aqueous layer was extracted with DCM (2×50 mL)
5. 5
   LavadoThe combined organic layers were washed with 5% NaHCO3 (2×30 mL), brine (30 mL)
6. 6
   Secadodried over Na2SO4
7. 7
   Filtraciónfiltered
8. 8
   Otroevaporated to dryness
9. 9
   Otroto yield a crude, which
10. 10
    Otrowas purified by flash chromatography (silica gel/hexanes:ethyl acetate 0-60%)

Procedimiento

To a vigorously stirring solution of N-Boc-3-methylene-cyclobutanamine (9.8 g, 53.5 mmol) in DCM (160 mL) and H2O (160 mL) was added K2CO3 (3 g, 21.7 mmol), followed by NaClO4 (35 g, 163.5 mmol), tetrabutylammonium chloride (0.2 g, 0.72 mmol) and RuCl3 (0.6 g, 7.6 mmol). During the course of the reaction, the organic solution turned dark brown, the catalyst turned black, while the upper aqueous layer turned white. The reaction was monitored by TLC, and upon completion, the reaction mixture was filtered through a pad of celite. The filtrates were transferred to a separatory funnel, and the aqueous layer was extracted with DCM (2×50 mL). The combined organic layers were washed with 5% NaHCO3 (2×30 mL), brine (30 mL), dried over Na2SO4, filtered and evaporated to dryness to yield a crude, which was purified by flash chromatography (silica gel/hexanes:ethyl acetate 0-60%) to yield the desired N-Boc-3-amino-cyclobutanone (7.13 g, 38.53 mmol, 72% yield): NMR (250 MHz, CDCl3) δ 4.88 (bs, 1H), 4.13-4.29 (m, 1H), 3.23-3.41 (m, 2H), 2.9-3.05 (m, 2H), 1.39 (s, 9H).

Fuente