تفاعل #155403

معادلة التفاعل

N-Boc-3-methylene-cyclobutanamine

K2CO3

→

N-Boc-3-amino-cyclobutanone

المردود 177.6%

المذيبات

DCM

H2O

ظروف التفاعل

المعالجة

1. 1
   أخرىDuring the course of the reaction
2. 2
   ترشيحupon completion, the reaction mixture was filtered through a pad of celite
3. 3
   أخرىThe filtrates were transferred to a separatory funnel
4. 4
   استخلاصthe aqueous layer was extracted with DCM (2×50 mL)
5. 5
   غسيلThe combined organic layers were washed with 5% NaHCO3 (2×30 mL), brine (30 mL)
6. 6
   تجفيفdried over Na2SO4
7. 7
   ترشيحfiltered
8. 8
   أخرىevaporated to dryness
9. 9
   أخرىto yield a crude, which
10. 10
    أخرىwas purified by flash chromatography (silica gel/hexanes:ethyl acetate 0-60%)

الإجراء التجريبي

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).

المصدر