ethyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.2]octane-3-carboxylate

Base Information

• Chemical Name: ethyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.2]octane-3-carboxylate
• CAS No.: 851389-16-7
• Molecular Formula: C₁₈H₂₅NO₄
• Molecular Weight: 319.401
• Mol file: 851389-16-7.mol

Synonyms:ethyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.2]octane-3-carboxylate

Chemical Property of ethyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.2]octane-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.2]octane-3-carboxylate

There total 1 articles about ethyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.2]octane-3-carboxylate 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:

exo-2-aza-2-<(R)-1-phenylethyl>-3-ethoxycarbonyl<2.2.2>bicyclooct-5-ene (134984-64-8) → ethyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.2]octane-3-carboxylate (851389-16-7)

Guidance literature:

With potassium dioxotetrahydroxoosmate(VI); potassium carbonate; potassium hexacyanoferrate(III); In tert-butyl alcohol; at 20 ℃; for 12h;

DOI:10.1055/s-2002-34901

Reference yield:

ethyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.2]octane-3-carboxylate (851389-16-7) → (6S,7S,9aS)-7-Formyl-1-hydroxy-4-oxo-octahydro-pyrido[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (508205-10-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 18.8 g / H₂ / Pd/C / ethanol / 24 h / 20 °C / 760 Torr

2: 71 percent / HOBt; DCC / dimethylformamide / 12 h / 20 °C

3: 65 percent / NaIO₄ / acetone; H₂O / 0.5 h / -25 °C

With sodium periodate; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1002/ejoc.200300700

Reference yield:

ethyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.2]octane-3-carboxylate (851389-16-7) → (1S,6S,7S,9aS)-1-Hydroxy-7-hydroxymethyl-4-oxo-octahydro-pyrido[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 18.8 g / H₂ / Pd/C / ethanol / 24 h / 20 °C / 760 Torr

2: 71 percent / HOBt; DCC / dimethylformamide / 12 h / 20 °C

3: 65 percent / NaIO₄ / acetone; H₂O / 0.5 h / -25 °C

4: 41 percent / NaBH₄ / methanol / 1 h / 0 °C

With sodium tetrahydroborate; sodium periodate; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; ethanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1002/ejoc.200300700

upstream raw materials:

exo-2-aza-2-<(R)-1-phenylethyl>-3-ethoxycarbonyl<2.2.2>bicyclooct-5-ene

Downstream raw materials:

(1S,2S,6R,7S,9S)-4,4-Dimethyl-8-((R)-1-phenyl-ethyl)-3,5-dioxa-8-aza-tricyclo[5.2.2.0^2,6]undecane-9-carboxylic acid ethyl ester

ethyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylate

(6S,7S,9aS)-7-Formyl-1-hydroxy-4-oxo-octahydro-pyrido[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester

ethyl (1S,3S,4S,5S,6R)-2-(2-benzyloxycarbonylaminoacetyl)-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylate