반응 #42942

반응 방정식

benzyl alcohol

triethylamine

(4-Azidocarbonyl-6,7-dimethoxy-isoquinolin-1-ylmethyl)-carbamic acid tert-butyl ester

EtOAc

→

desired product

수율 64.0%

[1-(tert-Butoxycarbonylamino-methyl)-6,7-dimethoxy-isoquinolin-4-yl]-carbamic acid benzyl ester

수율 64.0%

용매

toluene

NH4OH

반응 조건

후처리

1. 1
   workup.ADDITIONwere added
2. 2
   추출The aqueous phase was extracted with 20 mL EtOAc
3. 3
   세척the combined organics were washed with brine
4. 4
   건조dried over MgSO4
5. 5
   여과filtered though a 1-cm plug of silica
6. 6
   기타After removal of the solvent
7. 7
   기타the residue was purified by flash chromatography
8. 8
   세척eluting with a gradient of 1%-5% MeOH in DCM

실험 절차

A solution of (4-Azidocarbonyl-6,7-dimethoxy-isoquinolin-1-ylmethyl)-carbamic acid tert-butyl ester (1.36 g) in 40 mL of toluene was heated to 95° C. for 20 min, then the reaction flask was removed from the oil bath and benzyl alcohol (600 mg, 1.5 eq) and triethylamine (355 mg, 1.0 eq) were added. The reaction was allowed to stir at 80° C. After 3 h, TLC indicated clean conversion to a single product. The reaction was diluted with 30 mL EtOAc, and 25 mL 1% NH4OH. The aqueous phase was extracted with 20 mL EtOAc, and the combined organics were washed with brine, dried over MgSO4, and filtered though a 1-cm plug of silica. After removal of the solvent, the residue was purified by flash chromatography, eluting with a gradient of 1%-5% MeOH in DCM to give 1.05 g (64%) of the desired product. H1-NMR (CDCl3): δ 8.50 (br s, 1H), 7.3-7.5 (m, 1H), 6.75 (s, 1H), 6.12 (s, 1H), 5.24 (s, 2H), 4.82 (d, 1H), 4.00 (s, 3H), 3.91 (s, 3H), 1.49 (s, 9H).

출처