1-((1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carbonyl)-1,3-bis-((S)-1-phenyl-ethyl)-urea

Base Information

• Chemical Name: 1-((1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carbonyl)-1,3-bis-((S)-1-phenyl-ethyl)-urea
• CAS No.: 119945-16-3
• Molecular Formula: C₂₅H₂₈N₂O₂
• Molecular Weight: 388.51
• Mol file: 119945-16-3.mol

Synonyms:1-((1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carbonyl)-1,3-bis-((S)-1-phenyl-ethyl)-urea

Chemical Property of 1-((1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carbonyl)-1,3-bis-((S)-1-phenyl-ethyl)-urea

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-((1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carbonyl)-1,3-bis-((S)-1-phenyl-ethyl)-urea

There total 3 articles about 1-((1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carbonyl)-1,3-bis-((S)-1-phenyl-ethyl)-urea 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: 29.0%

N-((S)-1-phenylethyl)-N-((((S)-1-phenylethyl)amino)carbonyl)acrylamide (119908-37-1) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → 1-((1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carbonyl)-1,3-bis-((S)-1-phenyl-ethyl)-urea (119945-16-3) + 1-((1S,2R,4S)-Bicyclo[2.2.1]hept-5-ene-2-carbonyl)-1,3-bis-((S)-1-phenyl-ethyl)-urea (119945-15-2) + 1-((1S,2S,4S)-Bicyclo[2.2.1]hept-5-ene-2-carbonyl)-1,3-bis-((S)-1-phenyl-ethyl)-urea (119945-17-4) + 1-((1R,2S,4R)-Bicyclo[2.2.1]hept-5-ene-2-carbonyl)-1,3-bis-((S)-1-phenyl-ethyl)-urea (119908-39-3)

Guidance literature:

In toluene; at 100 ℃; for 3h; Yields of byproduct given;

DOI:10.1021/jo00271a036

Reference yield:

endo-norbornenecarboxylic acid (120-74-1,934-30-5,1195-12-6,20507-53-3,58001-99-3,67999-50-2,67999-53-5,74645-32-2,108266-75-7) + α-Trifluoromethyl-β-chloroethylsulfenyl chloride (87612-17-7) + bis<(S)-1-phenylethyl>carbodiimide (57122-22-2) → 4-(1-trifluoromethyl-2-chloroethylthio)-6-oxatricyclo<3.2.1.13,8>nonan-7-one (128856-03-1) + 1-((1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carbonyl)-1,3-bis-((S)-1-phenyl-ethyl)-urea (119945-16-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / LiAlH₄

2: 93 percent / pyridine

3: 1.) B₂H₆, 2.) NaOH, H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) 30 min

With sodium hydroxide; lithium aluminium tetrahydride; dihydrogen peroxide; diborane; In pyridine;

Reference yield:

bis<(S)-1-phenylethyl>carbodiimide (57122-22-2) → 1-((1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carbonyl)-1,3-bis-((S)-1-phenyl-ethyl)-urea (119945-16-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / Et₃N / acetonitrile / 24 h / Ambient temperature

2: toluene / 3 h / 100 °C

With triethylamine; In toluene; acetonitrile;

DOI:10.1021/jo00271a036

upstream raw materials:

endo-norbornenecarboxylic acid

α-Trifluoromethyl-β-chloroethylsulfenyl chloride

bis<(S)-1-phenylethyl>carbodiimide

N-((S)-1-phenylethyl)-N-((((S)-1-phenylethyl)amino)carbonyl)acrylamide