1-(2-hydroxy-1-(1R)-phenylethyl amino)-1-(8-(benzyloxycarbonyl)-8-aza-bicyclo[3.2.1]-oct-3-yl)-exo-methane-1-(1S)-carbo-nitrile

Base Information

• Chemical Name: 1-(2-hydroxy-1-(1R)-phenylethyl amino)-1-(8-(benzyloxycarbonyl)-8-aza-bicyclo[3.2.1]-oct-3-yl)-exo-methane-1-(1S)-carbo-nitrile
• CAS No.: 1266350-19-9
• Molecular Formula: C₂₁H₃₁N₃O₄
• Molecular Weight: 389.495
• Mol file: 1266350-19-9.mol

Synonyms:1-(2-hydroxy-1-(1R)-phenylethyl amino)-1-(8-(benzyloxycarbonyl)-8-aza-bicyclo[3.2.1]-oct-3-yl)-exo-methane-1-(1S)-carbo-nitrile

Chemical Property of 1-(2-hydroxy-1-(1R)-phenylethyl amino)-1-(8-(benzyloxycarbonyl)-8-aza-bicyclo[3.2.1]-oct-3-yl)-exo-methane-1-(1S)-carbo-nitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2-hydroxy-1-(1R)-phenylethyl amino)-1-(8-(benzyloxycarbonyl)-8-aza-bicyclo[3.2.1]-oct-3-yl)-exo-methane-1-(1S)-carbo-nitrile

There total 7 articles about 1-(2-hydroxy-1-(1R)-phenylethyl amino)-1-(8-(benzyloxycarbonyl)-8-aza-bicyclo[3.2.1]-oct-3-yl)-exo-methane-1-(1S)-carbo-nitrile 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: 32.0%

methyl (2S)-8-azabicyclo[3.2.1]oct-3-yl[(2-hydroxy-1-(1R)-phenylethyl)amino]-exo-acetate hydrochloride salt + N,N-Dimethylcarbamoyl chloride (79-44-7) → 1-(2-hydroxy-1-(1R)-phenylethyl amino)-1-(8-(benzyloxycarbonyl)-8-aza-bicyclo[3.2.1]-oct-3-yl)-exo-methane-1-(1S)-carbo-nitrile (1266350-19-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 16h;

Reference yield:

benzyl 3-formyl-8-azabicyclo[3.2.1]octane-8-carboxylate (952423-57-3) → 1-(2-hydroxy-1-(1R)-phenylethyl amino)-1-(8-(benzyloxycarbonyl)-8-aza-bicyclo[3.2.1]-oct-3-yl)-exo-methane-1-(1S)-carbo-nitrile (1266350-19-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetic acid / methanol / 0.5 h / 20 °C / Inert atmosphere

1.2: 2 h / 20 °C

2.1: hydrogenchloride / methanol / 32 h / 20 °C

3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C

With hydrogenchloride; acetic acid; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide; 1.1: Strecker Synthesis;

Reference yield:

benzyl (1R,5S)-3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate → 1-(2-hydroxy-1-(1R)-phenylethyl amino)-1-(8-(benzyloxycarbonyl)-8-aza-bicyclo[3.2.1]-oct-3-yl)-exo-methane-1-(1S)-carbo-nitrile (1266350-19-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide; hexane / 1.75 h / 20 °C

2.1: boron trifluoride diethyl etherate / dichloromethane / 2.5 h / 20 °C

3.1: acetic acid / methanol / 0.5 h / 20 °C / Inert atmosphere

3.2: 2 h / 20 °C

4.1: hydrogenchloride / methanol / 32 h / 20 °C

5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 0 - 20 °C

With hydrogenchloride; boron trifluoride diethyl etherate; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; In methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 3.1: Strecker Synthesis;

upstream raw materials:

N,N-Dimethylcarbamoyl chloride

tropinone

benzyl 3-formyl-8-azabicyclo[3.2.1]octane-8-carboxylate

1-(2-hydroxy-1-(1R)-phenylethyl amino)-1-(8-(benzyloxy carbonyl)-8-aza-bicyclo[3.2.1]-oct-3-yl)-exo-methane-1-(1S)-carbonitrile hydrochloride salt