[(R)-1-(3-Azido-propyl)-2-methoxy-cyclohexa-2,5-dienyl]-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone

Base Information

• Chemical Name: [(R)-1-(3-Azido-propyl)-2-methoxy-cyclohexa-2,5-dienyl]-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone
• CAS No.: 171523-91-4
• Molecular Formula: C₁₇H₂₆N₄O₃
• Molecular Weight: 334.418
• Mol file: 171523-91-4.mol

Synonyms:[(R)-1-(3-Azido-propyl)-2-methoxy-cyclohexa-2,5-dienyl]-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone

Chemical Property of [(R)-1-(3-Azido-propyl)-2-methoxy-cyclohexa-2,5-dienyl]-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(R)-1-(3-Azido-propyl)-2-methoxy-cyclohexa-2,5-dienyl]-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone

There total 1 articles about [(R)-1-(3-Azido-propyl)-2-methoxy-cyclohexa-2,5-dienyl]-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone 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: 88.0%

1-azido-3-iodopropane (58503-62-1) + (S)-2-methoxy-1-[[2'-(methoxymethyl)pyrrolidinyl]carbonyl]benzene (102069-84-1) → [(R)-1-(3-Azido-propyl)-2-methoxy-cyclohexa-2,5-dienyl]-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone (171523-91-4)

Guidance literature:

With penta-1,3-diene; ammonia; tert-butyl alcohol; In tetrahydrofuran; -78 deg C, 30 min., -78 deg C, 3 h;

DOI:10.1021/jo00129a052

Reference yield: 82.0%

[(R)-1-(3-Azido-propyl)-2-methoxy-cyclohexa-2,5-dienyl]-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone (171523-91-4) → (R)-2-(3-Azido-propyl)-2-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-cyclohex-3-enone (171523-73-2)

Guidance literature:

With hydrogenchloride; In methanol; for 18h; Ambient temperature;

DOI:10.1021/jo00129a052

Reference yield:

[(R)-1-(3-Azido-propyl)-2-methoxy-cyclohexa-2,5-dienyl]-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone (171523-91-4) → (7aS,8S,9R,11aS)-1,2,5,6,10,11-Hexahydro-7H-3-oxo-7a-(benzyloxycarbonyl)-8,9-epoxypyrrolo<2,1-j>quinoline

Guidance literature:

Multi-step reaction with 6 steps

1: 82 percent / 6N aq. HCl / methanol / 18 h / Ambient temperature

2: 95 percent / I₂ / tetrahydrofuran; H₂O / 24 h / Ambient temperature

3: 60 percent / SnCl₂, NaHCO₃ / dioxane; H₂O / 1.) 7 h, room temp., 2.) 45 min.

4: 84 percent / n-BuLi / tetrahydrofuran / 1.) 0 deg C, 15 min., 2.) - 78 deg to r.t., overnight

5: 42 percent / NaHCO₃ / tetrahydrofuran / 2.5 h / 0 °C

6: n-BuSnH, AIBN / benzene / Heating

With hydrogenchloride; n-butyllithium; n-butyl tin hydride; 2,2'-azobis(isobutyronitrile); iodine; sodium hydrogencarbonate; tin(ll) chloride; In tetrahydrofuran; 1,4-dioxane; methanol; water; benzene;

DOI:10.1021/jo00129a052

upstream raw materials:

1-azido-3-iodopropane

(S)-2-methoxy-1-[[2'-(methoxymethyl)pyrrolidinyl]carbonyl]benzene

Downstream raw materials:

(R)-2-(3-Azido-propyl)-2-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-cyclohex-3-enone

(4aR,5S,6R)-5,6-Epoxy-2,3,7,8-tetrahydro-4H-4a-(benzyloxycarbonyl)quinoline

(4aR,5R,6R)-N-(2-Bromoacetyl)-5-iodo-1,2,3,4,4a,5,6,7-octahydroquinoline-4a,6-carbolactone

(4aR,5R,6R)-N-(3-Bromopropionyl)-5-iodo-2,3-dihydro-4H,7H-quinoline-4a,6-carbolactone