N-[7,9-dihydroxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.0^1.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl ester

Base Information

• Chemical Name: N-[7,9-dihydroxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.0^1.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl ester
• CAS No.: 844857-13-2
• Molecular Formula: C₂₅H₃₈N₂O₅
• Molecular Weight: 446.587
• Mol file: 844857-13-2.mol

Synonyms:N-[7,9-dihydroxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.0^1.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl ester

Chemical Property of N-[7,9-dihydroxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.0^1.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[7,9-dihydroxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.0^1.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl ester

There total 21 articles about N-[7,9-dihydroxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.0^1.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

N-[7,9-bisbenzyloxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.01.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl ester (844857-25-6) → N-[7,9-dihydroxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.01.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl ester (844857-13-2)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; for 12h; under 2585.74 Torr;

DOI:10.1021/jo0483567

Reference yield:

cyclohexanedione monoethylene ketal (4746-97-8) → N-[7,9-dihydroxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.01.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl ester (844857-13-2)

Guidance literature:

Multi-step reaction with 19 steps

1.1: iPr₂NH; n-BuLi / tetrahydrofuran; hexane / 0.67 h / -78 °C

1.2: ZnCl₂ / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.3: 56 percent / tetrahydrofuran; hexane / 0.33 h / -78 °C

2.1: 71 percent / Bu₄NI; Ag₂O / 12 h / 20 °C

3.1: 2,6-lutidine; TBDMSOTf / CH₂Cl₂ / 0 - 20 °C

3.2: 96 percent / TBAF / tetrahydrofuran / 0.17 h / 0 °C

4.1: 1-(3-dimethylamino)propyl-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 3 h / 20 °C

5.1: TBAF / tetrahydrofuran / 0.5 h / 0 °C

6.1: 96 percent / Ag₂O; CaSO₄ / 12 h / 20 °C

7.1: 97 percent / LiAlH₄ / toluene / 2 h / 80 °C

8.1: 90 percent / HCl / tetrahydrofuran / 12 h / 20 °C

9.1: p-TsOH / benzene / 3 h / Heating

10.1: L-phenylalanine / benzene / 2 h / Heating

10.2: 9.0 mg / NaBH₄; MeOH / tetrahydrofuran / -78 - 20 °C

11.1: CrO₃; H₂SO₄ / acetone / 5 h / 20 °C

12.1: Et₃N / acetone / 1 h / 0 °C

13.1: NaN₃ / acetone; H₂O / 1.25 h / 0 - 20 °C

14.1: toluene / 0.75 h / 90 °C

15.1: toluene / 6 h / 90 °C

16.1: 82 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

17.1: 90 percent / Et₃N / ethyl acetate / 7 h / 20 °C

18.1: 78 percent / H₂ / Pd(OH)2/C / methanol / 12 h / 2585.74 Torr

With 2,6-dimethylpyridine; chromium(VI) oxide; hydrogenchloride; calcium sulfate; lithium aluminium tetrahydride; n-butyllithium; sodium azide; L-phenylalanine; sulfuric acid; t-butyldimethylsiyl triflate; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; diisopropylamine; silver(l) oxide; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; acetone; toluene; benzene; 2.1: Luche reduction / 15.1: Curtius rearrangement;

DOI:10.1021/jo0483567

Reference yield:

N-t-butoxylcarbonyl-O-methyl-L-tyrosinal (139183-60-1) → N-[7,9-dihydroxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.01.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl ester (844857-13-2)

Guidance literature:

Multi-step reaction with 19 steps

1.1: iPr₂NH; n-BuLi / tetrahydrofuran; hexane / 0.67 h / -78 °C

1.2: ZnCl₂ / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.3: 56 percent / tetrahydrofuran; hexane / 0.33 h / -78 °C

2.1: 71 percent / Bu₄NI; Ag₂O / 12 h / 20 °C

3.1: 2,6-lutidine; TBDMSOTf / CH₂Cl₂ / 0 - 20 °C

3.2: 96 percent / TBAF / tetrahydrofuran / 0.17 h / 0 °C

4.1: 1-(3-dimethylamino)propyl-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 3 h / 20 °C

5.1: TBAF / tetrahydrofuran / 0.5 h / 0 °C

6.1: 96 percent / Ag₂O; CaSO₄ / 12 h / 20 °C

7.1: 97 percent / LiAlH₄ / toluene / 2 h / 80 °C

8.1: 90 percent / HCl / tetrahydrofuran / 12 h / 20 °C

9.1: p-TsOH / benzene / 3 h / Heating

10.1: L-phenylalanine / benzene / 2 h / Heating

10.2: 9.0 mg / NaBH₄; MeOH / tetrahydrofuran / -78 - 20 °C

11.1: CrO₃; H₂SO₄ / acetone / 5 h / 20 °C

12.1: Et₃N / acetone / 1 h / 0 °C

13.1: NaN₃ / acetone; H₂O / 1.25 h / 0 - 20 °C

14.1: toluene / 0.75 h / 90 °C

15.1: toluene / 6 h / 90 °C

16.1: 82 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

17.1: 90 percent / Et₃N / ethyl acetate / 7 h / 20 °C

18.1: 78 percent / H₂ / Pd(OH)2/C / methanol / 12 h / 2585.74 Torr

With 2,6-dimethylpyridine; chromium(VI) oxide; hydrogenchloride; calcium sulfate; lithium aluminium tetrahydride; n-butyllithium; sodium azide; L-phenylalanine; sulfuric acid; t-butyldimethylsiyl triflate; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; diisopropylamine; silver(l) oxide; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; acetone; toluene; benzene; 2.1: Luche reduction / 15.1: Curtius rearrangement;

DOI:10.1021/jo0483567

upstream raw materials:

N-[7,9-bisbenzyloxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.0^1.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl ester

cyclohexanedione monoethylene ketal

di-tert-butyl dicarbonate

N-t-butoxylcarbonyl-O-methyl-L-tyrosinal

Downstream raw materials:

N-[9-(bisbenzyloxyphosphoryloxy)-7-hydroxy-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.0^1.5]dodec-3-yl]-N-methylcarbamic acid tert-butyl ester