تفاعل #1702034

معادلة التفاعل

HCl

diisopropylethylamine

acetyl bromide

5

3-Methoxydodecanal

AlMe3

→

6

المردود 77.3%

(4R)-4-((2RS)-2-Methoxyundecyl)oxetan-2-one

المردود 77.3%

المذيبات

CH2Cl2

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled to −45° C.
2. 2
   workup.STIRRINGThe resulting pale yellow solution was stirred for 14 h at −45° C.
3. 3
   درجة الحرارةwarmed to rt
4. 4
   workup.ADDITIONpoured into a separatory funnel
5. 5
   غسيلThe organic layer was washed with saturated NaHCO3, brine
6. 6
   تجفيفdried (Na2SO4)
7. 7
   أخرىThe solvent was removed in vacuo
8. 8
   أخرىthe yellow oily product was purified by chromatography on SiO2 (4% EtOAc/hexanes to 6% EtOAc/hexanes)

الإجراء التجريبي

A solution of N,N′-(1R,1′R)-1,1′-(benzylazanediyl)bis(2-methylpropane-1,1-diyl)bis(1,1,1-trifluoromethanesulfonamide) (81.2 mg, 0.15 mmol, 30 mol %) in CH2Cl2 (1 mL) was treated at rt under N2 slowly with a solution of AlMe3 (10.8 mg, 0.15 mmol) in CH2Cl2 (0.5 mL). The mixture was stirred at room temperature (rt) for 2 h, cooled to −45° C. and treated sequentially with diisopropylethylamine (11 mg, 1.7 equiv), acetyl bromide (117 mg, 1.9 equiv) and 5 (107 mg, 0.500 mmol, 1.0 equiv). The resulting pale yellow solution was stirred for 14 h at −45° C., warmed to rt, and poured into a separatory funnel containing 0.1 N HCl (10) mL). The organic layer was washed with saturated NaHCO3, brine, and dried (Na2SO4). The solvent was removed in vacuo and the yellow oily product was purified by chromatography on SiO2 (4% EtOAc/hexanes to 6% EtOAc/hexanes) to give 6 (99.1 mg, 77%) as a colorless oil: 1H NMR (CDCl3) 4.8-4.65 (m, 1H), 3.60-3.50 (m, 1H), 3.3-3.2 (m, 1H), 3.35, 3.32 (2s, 3H), 3.22-3.08 (m, 1H), 2.18-1.82 (m, 2H) 1.65-1.35 (m, 2H), 1.35-1.20 (m, 14H), 0.90-0.80 (m, 3H).

المصدر