반응 #797098

반응 방정식

benzylamine

6-(benzyloxy)-3,4-dihydronaphthalen-2-ylboronic acid

ethanol

1,3-Dihydroxy-2-propanone

→

product

수율 15.0%

2-(Benzylamino)-2-(6-(benzyloxy)-3,4-dihydronaphthalen-2-yl)propane-1,3-diol

수율 15.0%

용매

DCM MeOH

반응 조건

후처리

1. 1
   여과The mixture was filtered
2. 2
   농축The filtrate was concentrated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in EtOAc/MeOH (300 mL/30 mL)
4. 4
   세척washed with saturated NaHCO3/water (50 mL/50 mL)
5. 5
   추출the aqueous layer was extracted with EtOAc (2×50 mL)
6. 6
   세척The combined organic layers were washed with water (50 mL), brine
7. 7
   건조dried with Na2SO4
8. 8
   여과filtered
9. 9
   농축concentrated
10. 10
    기타dried in high vacuum
11. 11
    기타to give a red-brown solid product as the first crop
12. 12
    workup.STIRRINGstirred at r.t. overnight under an atmosphere of nitrogen
13. 13
    농축The solution was concentrated
14. 14
    workup.ADDITIONThe residue was treated as the first crop with EtOAc-MeOH-aqueous NaHCO3

실험 절차

The intermediate, 6-(benzyloxy)-3,4-dihydronaphthalen-2-ylboronic acid, from previous step was dissolved in ethanol (400 mL, 7 mol). 1,3-Dihydroxy-2-propanone (6.22 g, 0.0690 mol) was added followed by benzylamine (7.54 mL, 0.0690 mol). The solution turned into a yellow suspension in 1 min. The mixture was stirred at r.t. for 2 hours under an atmosphere of nitrogen. The mixture was filtered. The filtrate was concentrated and the residue was dissolved in EtOAc/MeOH (300 mL/30 mL), washed with saturated NaHCO3/water (50 mL/50 mL) and the aqueous layer was extracted with EtOAc (2×50 mL). The combined organic layers were washed with water (50 mL), brine, dried with Na2SO4, filtered, concentrated and dried in high vacuum to give a red-brown solid product as the first crop. The collected solid was dissolved in DCM-MeOH (50 ml/50 mL) and stirred at r.t. overnight under an atmosphere of nitrogen. The solution was concentrated. The residue was treated as the first crop with EtOAc-MeOH-aqueous NaHCO3 to afford the second crop of product (4.40 g, 15%). 1H NMR (CHLOROFORM-d) δ: 6.98-7.66 (m, 13H), 6.77 (br. s., 1H), 5.05 (br. s., 2H), 3.75-4.21 (m, 6H), 2.78 (m, 2H), 1.88-2.54 (m, 2H). MS (M+1): 416.0.

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