[(1S,3S,6S,7S,8R)-7-Hydroxy-6-(4-methoxy-benzyl)-9-oxo-5-aza-tricyclo[6.3.1.0^1,5]dodec-3-yl]-methyl-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(1S,3S,6S,7S,8R)-7-Hydroxy-6-(4-methoxy-benzyl)-9-oxo-5-aza-tricyclo[6.3.1.0^1,5]dodec-3-yl]-methyl-carbamic acid tert-butyl ester
• CAS No.: 327037-80-9
• Molecular Formula: C₂₅H₃₆N₂O₅
• Molecular Weight: 444.571

Synonyms:[(1S,3S,6S,7S,8R)-7-Hydroxy-6-(4-methoxy-benzyl)-9-oxo-5-aza-tricyclo[6.3.1.0^1,5]dodec-3-yl]-methyl-carbamic acid tert-butyl ester

Chemical Property of [(1S,3S,6S,7S,8R)-7-Hydroxy-6-(4-methoxy-benzyl)-9-oxo-5-aza-tricyclo[6.3.1.0^1,5]dodec-3-yl]-methyl-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of [(1S,3S,6S,7S,8R)-7-Hydroxy-6-(4-methoxy-benzyl)-9-oxo-5-aza-tricyclo[6.3.1.0^1,5]dodec-3-yl]-methyl-carbamic acid tert-butyl ester

There total 14 articles about [(1S,3S,6S,7S,8R)-7-Hydroxy-6-(4-methoxy-benzyl)-9-oxo-5-aza-tricyclo[6.3.1.0^1,5]dodec-3-yl]-methyl-carbamic 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: 34.0%

{(S)-1-[(S)-1-Formyl-2-(4-methoxy-phenyl)-ethyl]-8-oxo-1-aza-spiro[4.5]dec-3-yl}-methyl-carbamic acid tert-butyl ester (327037-79-6) → [(1R,3S,6S,8S)-7-Hydroxy-6-(4-methoxy-benzyl)-9-oxo-5-aza-tricyclo[6.3.1.01,5]dodec-3-yl]-methyl-carbamic acid tert-butyl ester + [(1S,3S,6S,7R,8R)-7-Hydroxy-6-(4-methoxy-benzyl)-9-oxo-5-aza-tricyclo[6.3.1.01,5]dodec-3-yl]-methyl-carbamic acid tert-butyl ester + [(1S,3S,6S,7S,8R)-7-Hydroxy-6-(4-methoxy-benzyl)-9-oxo-5-aza-tricyclo[6.3.1.01,5]dodec-3-yl]-methyl-carbamic acid tert-butyl ester (327037-80-9)

Guidance literature:

With sodium methylate; In methanol; at 0 ℃; for 2h;

DOI:10.1002/1521-3773(20001215)39:24<4593::AID-ANIE4593>3.0.CO;2-X

Reference yield:

methyl (S)-2-amino-3-(4-methoxyphenyl)propionate (17355-19-0) → [(1S,3S,6S,7S,8R)-7-Hydroxy-6-(4-methoxy-benzyl)-9-oxo-5-aza-tricyclo[6.3.1.01,5]dodec-3-yl]-methyl-carbamic acid tert-butyl ester (327037-80-9)

Guidance literature:

Multi-step reaction with 8 steps

1: NaBH(OAc)3; molecular sieves 4 Angstroem / 25 h / 0 - 20 °C

2: 51 percent / PhI(OAc)2 / various solvent(s) / 0.17 h / 20 °C

3: NaSPh / dimethylsulfoxide / 3 h / 20 °C

4: pyridine / 12 h / 20 °C

5: 93 percent / H₂ / Raney Ni / ethanol; ethyl acetate / 15 h / 20 °C

6: 90 percent / LiAlH₄ / tetrahydrofuran / 3 h / -78 - 0 °C

7: 100 percent / (COCl)2; DMSO; DIEA / CH₂Cl₂ / 0.5 h / -78 °C

8: 34 percent / NaOMe / methanol / 2 h / 0 °C

With pyridine; lithium aluminium tetrahydride; oxalyl dichloride; [bis(acetoxy)iodo]benzene; 4 A molecular sieve; hydrogen; sodium methylate; sodium thiophenolate; sodium tris(acetoxy)borohydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; nickel; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; 7: Swern oxidation;

DOI:10.1002/1521-3773(20001215)39:24<4593::AID-ANIE4593>3.0.CO;2-X

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → [(1S,3S,6S,7S,8R)-7-Hydroxy-6-(4-methoxy-benzyl)-9-oxo-5-aza-tricyclo[6.3.1.01,5]dodec-3-yl]-methyl-carbamic acid tert-butyl ester (327037-80-9)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 12 h / 20 °C

2: 93 percent / H₂ / Raney Ni / ethanol; ethyl acetate / 15 h / 20 °C

3: 90 percent / LiAlH₄ / tetrahydrofuran / 3 h / -78 - 0 °C

4: 100 percent / (COCl)2; DMSO; DIEA / CH₂Cl₂ / 0.5 h / -78 °C

5: 34 percent / NaOMe / methanol / 2 h / 0 °C

With pyridine; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; sodium methylate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; nickel; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; 4: Swern oxidation;

DOI:10.1002/1521-3773(20001215)39:24<4593::AID-ANIE4593>3.0.CO;2-X

upstream raw materials:

{(S)-1-[(S)-1-Formyl-2-(4-methoxy-phenyl)-ethyl]-8-oxo-1-aza-spiro[4.5]dec-3-yl}-methyl-carbamic acid tert-butyl ester

di-tert-butyl dicarbonate

methyl (S)-2-amino-3-(4-methoxyphenyl)propionate

N-[1-formyl-2-(4-hydroxy-phenyl)-ethyl]-N-methyl-4-nitro-benzenesulfonamide

Downstream raw materials:

[(1S,3S,6S,7S,8S,9R)-7,9-Dihydroxy-6-(4-methoxy-benzyl)-5-aza-tricyclo[6.3.1.0^1,5]dodec-3-yl]-methyl-carbamic acid tert-butyl ester

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

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