(5R,4'S)-4-benzyl-7,7-dibromo-5-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-6-methoxy-3-oxa-4-azabicyclo[4.1.0]heptane

Base Information

• Chemical Name: (5R,4'S)-4-benzyl-7,7-dibromo-5-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-6-methoxy-3-oxa-4-azabicyclo[4.1.0]heptane
• CAS No.: 869367-94-2
• Molecular Formula: C₁₈H₂₃Br₂NO₄
• Molecular Weight: 477.193
• Mol file: 869367-94-2.mol

Synonyms:(5R,4'S)-4-benzyl-7,7-dibromo-5-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-6-methoxy-3-oxa-4-azabicyclo[4.1.0]heptane

Chemical Property of (5R,4'S)-4-benzyl-7,7-dibromo-5-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-6-methoxy-3-oxa-4-azabicyclo[4.1.0]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,4'S)-4-benzyl-7,7-dibromo-5-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-6-methoxy-3-oxa-4-azabicyclo[4.1.0]heptane

There total 1 articles about (5R,4'S)-4-benzyl-7,7-dibromo-5-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-6-methoxy-3-oxa-4-azabicyclo[4.1.0]heptane 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: 65.0%

Bromoform (75-25-2) + (3R,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine (227622-64-2) → (5R,4'S)-4-benzyl-7,7-dibromo-5-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-6-methoxy-3-oxa-4-azabicyclo[4.1.0]heptane (869367-94-2)

Guidance literature:

With potassium fluoride; sodium hydroxide; at 20 ℃; for 48h;

DOI:10.1055/s-2005-872667

Reference yield: 53.0%

(5R,4'S)-4-benzyl-7,7-dibromo-5-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-6-methoxy-3-oxa-4-azabicyclo[4.1.0]heptane (869367-94-2) + methanol (67-56-1) → (3R,4'S)-2-benzyl-5-bromo-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4,4-dimethoxy-2,3,4,7-tetrahydro-1,2-oxazepine (869367-96-4)

Guidance literature:

With potassium carbonate; for 20h; Heating;

DOI:10.1055/s-2005-872667

Reference yield:

(5R,4'S)-4-benzyl-7,7-dibromo-5-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-6-methoxy-3-oxa-4-azabicyclo[4.1.0]heptane (869367-94-2) → (3R,4'S)-2-benzyl-4,4-dimethoxy-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-5-(3-methoxyprop-1-yn-1-yl)-2,3,4,7-tetrahydro[1,2]oxazepine

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / K₂CO₃ / 20 h / Heating

2: 74 percent / PPh₃; CuI; i-Pr₂NH / Pd(OAc)2 / dimethylformamide / 10 h / 20 °C

With copper(l) iodide; potassium carbonate; diisopropylamine; triphenylphosphine; palladium diacetate; In N,N-dimethyl-formamide; 2: Sonogashira reaction;

DOI:10.1055/s-2005-872667

upstream raw materials:

Bromoform

(3R,4'S)-2-benzyl-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methoxy-3,6-dihydro-2H-1,2-oxazine

Downstream raw materials:

(3R,4'S)-2-benzyl-5-bromo-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4,4-dimethoxy-2,3,4,7-tetrahydro-1,2-oxazepine