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

Base Information

• Chemical Name: 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
• CAS No.: 1266350-13-3
• Molecular Formula: C₂₅H₂₉N₃O₃*ClH
• Molecular Weight: 455.984
• Mol file: 1266350-13-3.mol

Synonyms: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

Chemical Property of 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

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

There total 4 articles about 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 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: 42.0%

benzyl 3-formyl-8-azabicyclo[3.2.1]octane-8-carboxylate (952423-57-3) + trimethylsilyl cyanide (7677-24-9) + D-2-phenylglycinol (56613-80-0) → 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 (1266350-13-3)

Guidance literature:

benzyl 3-formyl-8-azabicyclo[3.2.1]octane-8-carboxylate; D-2-phenylglycinol; With acetic acid; In methanol; at 20 ℃; for 0.5h; Inert atmosphere;

trimethylsilyl cyanide; In methanol; at 20 ℃; for 2h;

With hydrogenchloride; In methanol; Product distribution / selectivity;

Reference yield:

tropinone (532-24-1) → 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 (1266350-13-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / toluene; water / 2 h / Reflux

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

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

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

4.2: 2 h / 20 °C

With boron trifluoride diethyl etherate; sodium hydride; potassium carbonate; acetic acid; In methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 4.1: 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-(benzyloxy carbonyl)-8-aza-bicyclo[3.2.1]-oct-3-yl)-exo-methane-1-(1S)-carbonitrile hydrochloride salt (1266350-13-3)

Guidance literature:

Multi-step reaction with 3 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

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

upstream raw materials:

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

trimethylsilyl cyanide

D-2-phenylglycinol

tropinone

Downstream raw materials:

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

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