(1R,3R,4S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]hept-5-ene

Base Information

• Chemical Name: (1R,3R,4S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]hept-5-ene
• CAS No.: 187039-25-4
• Molecular Formula: C₁₈H₂₃NO₂
• Molecular Weight: 285.386
• Mol file: 187039-25-4.mol

Synonyms:(1R,3R,4S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]hept-5-ene

Chemical Property of (1R,3R,4S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]hept-5-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,4S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]hept-5-ene

There total 1 articles about (1R,3R,4S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]hept-5-ene 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:

benzylamine hydrochloride (3287-99-8,39110-74-2,108321-65-9) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + 2,3-isopropylidene-glyceraldehyde (15186-48-8) → (1R,3R,4S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]hept-5-ene (187039-25-4) + (1S,3R,4R)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]hept-5-ene + (1S,3S,4R)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]hept-5-ene

Guidance literature:

With neodymium(III) trifluoromethanesufonate; In water; for 48h; Product distribution; various lanthanide triflates Ln(OTf)3 (Ln = La, Pr, Gd, Dy, Er, Yb); aza Diels-Alder reaction of chiral aldehydes with benzylamine hydrochloride and cyclopentadiene, promoted by lanthanide triflates; exo/endo selectivity; diastereoselectivity;

DOI:10.1021/jo962074s

Reference yield: 84.0%

(1R,3R,4S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]hept-5-ene (187039-25-4) → (1R,3R,4R,5R,6S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]heptane-5,6-diol (187039-32-3)

Guidance literature:

With pyridine; osmium(VIII) oxide; trimethylamine-N-oxide; In water; isopropyl alcohol; Heating;

DOI:10.1021/jo962074s

Reference yield:

(1R,3R,4S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]hept-5-ene (187039-25-4) → (1R,3R,4R,5R,6S)-2-Benzyl-3-((S)-1,2-dihydroxy-ethyl)-2-aza-bicyclo[2.2.1]heptane-5,6-diol

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / OsO₄, trimethylamine oxide, pyridine / propan-2-ol; H₂O / Heating

2: 90 percent / AcOH, H₂O / 10 h / 55 °C

With pyridine; osmium(VIII) oxide; trimethylamine-N-oxide; water; acetic acid; In water; isopropyl alcohol;

DOI:10.1021/jo962074s

upstream raw materials:

benzylamine hydrochloride

cyclopenta-1,3-diene

2,3-isopropylidene-glyceraldehyde

Downstream raw materials:

(1R,3R,4R,5R,6S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]heptane-5,6-diol