(1R,5S,6R)-6-Dibenzylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid vinyl ester

Base Information

• Chemical Name: (1R,5S,6R)-6-Dibenzylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid vinyl ester
• CAS No.: 210165-63-2
• Molecular Formula: C₂₂H₂₄N₂O₂
• Molecular Weight: 348.445
• Mol file: 210165-63-2.mol

Synonyms:(1R,5S,6R)-6-Dibenzylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid vinyl ester

Chemical Property of (1R,5S,6R)-6-Dibenzylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid vinyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,5S,6R)-6-Dibenzylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid vinyl ester

There total 2 articles about (1R,5S,6R)-6-Dibenzylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid vinyl ester 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:

Dibenzyl-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-amine (164799-10-4) → (1R,5S,6R)-6-Dibenzylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid vinyl ester (210165-63-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / NCS / CH₂Cl₂ / 3 h / -78 - -30 °C

2: 95 percent / MeONa / 20 h / 20 °C

3: 89 percent / DIBAH / tetrahydrofuran / 1.) 60 deg C, 5 h, 2.) 20 deg C, 3 d

4: 50 percent / CHCl₃ / 1.) 50 deg C, 1.75 h, 2.) 20 deg C, 2 h

With N-chloro-succinimide; sodium methylate; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; chloroform;

DOI:10.1055/s-1998-2055

Reference yield:

Dibenzyl-(1-benzyl-3-chloro-1,2,3,6-tetrahydro-pyridin-4-yl)-amine (210165-61-0) → (1R,5S,6R)-6-Dibenzylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid vinyl ester (210165-63-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / MeONa / 20 h / 20 °C

2: 89 percent / DIBAH / tetrahydrofuran / 1.) 60 deg C, 5 h, 2.) 20 deg C, 3 d

3: 50 percent / CHCl₃ / 1.) 50 deg C, 1.75 h, 2.) 20 deg C, 2 h

With sodium methylate; diisobutylaluminium hydride; In tetrahydrofuran; chloroform;

DOI:10.1055/s-1998-2055

Reference yield: 74.0%

(1R,5S,6R)-6-Dibenzylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid vinyl ester (210165-63-2) → 1α,5α,6β-6-dibenzylamino-3-azabicyclo[3.1.0]hexane (210165-65-4)

Guidance literature:

With hydrogenchloride; water; In chloroform; for 14h; Ambient temperature;

DOI:10.1055/s-1998-2055

upstream raw materials:

Dibenzyl-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-amine

Dibenzyl-(1-benzyl-3-chloro-1,2,3,6-tetrahydro-pyridin-4-yl)-amine

Downstream raw materials:

1α,5α,6β-6-dibenzylamino-3-azabicyclo[3.1.0]hexane

7-((1R,5S,6R)-6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester

7-((1R,5S,6R)-6-Dibenzylamino-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester

7-((1R,5S,6R)-6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid; compound with methanesulfonic acid