2-[(2R,3S)-3-dibenzylamino-2-hydroxybutyl]cyclohex-2-enone ethylene acetal

Base Information

• Chemical Name: 2-[(2R,3S)-3-dibenzylamino-2-hydroxybutyl]cyclohex-2-enone ethylene acetal
• CAS No.: 864268-98-4
• Molecular Formula: C₂₆H₃₃NO₃
• Molecular Weight: 407.553
• Mol file: 864268-98-4.mol

Synonyms:2-[(2R,3S)-3-dibenzylamino-2-hydroxybutyl]cyclohex-2-enone ethylene acetal

Chemical Property of 2-[(2R,3S)-3-dibenzylamino-2-hydroxybutyl]cyclohex-2-enone ethylene acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(2R,3S)-3-dibenzylamino-2-hydroxybutyl]cyclohex-2-enone ethylene acetal

There total 1 articles about 2-[(2R,3S)-3-dibenzylamino-2-hydroxybutyl]cyclohex-2-enone ethylene acetal 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: 75.0%

6-bromo-1,4-dioxaspiro[4,5]dec-6-ene (70156-98-8) + (1R)-[1'(S)-(dibenzylamino)ethyl]oxirane (127927-41-7) → 2-[(2R,3S)-3-dibenzylamino-2-hydroxybutyl]cyclohex-2-enone ethylene acetal (864268-98-4)

Guidance literature:

6-bromo-1,4-dioxaspiro[4,5]dec-6-ene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h;

(1S)-[1'(S)-(dibenzylamino)ethyl]oxirane; With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

DOI:10.1016/j.tet.2005.06.024

Reference yield:

2-[(2R,3S)-3-dibenzylamino-2-hydroxybutyl]cyclohex-2-enone ethylene acetal (864268-98-4) → 1-Butyl-2-((2R,3S)-3-dibenzylamino-2-hydroxy-butyl)-cyclohex-2-enol

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine; DMAP / 20 °C

2: 80 mg / aq. HCl / tetrahydrofuran / 1 h / 20 °C

3: tetrahydrofuran; hexane / 4 h / -78 - 20 °C

With pyridine; hydrogenchloride; dmap; In tetrahydrofuran; hexane;

DOI:10.1016/j.tet.2005.06.024

Reference yield:

2-[(2R,3S)-3-dibenzylamino-2-hydroxybutyl]cyclohex-2-enone ethylene acetal (864268-98-4) → 2-[(2R,3S)-2-acetoxy-3-(dibenzylamino)butyl]-1-butylcyclohex-2-en-1-ol (864269-05-6)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine; DMAP / 20 °C

2: 80 mg / aq. HCl / tetrahydrofuran / 1 h / 20 °C

3: tetrahydrofuran; hexane / 4 h / -78 - 20 °C

4: 81 mg / pyridine; DMAP / 20 °C

With pyridine; hydrogenchloride; dmap; In tetrahydrofuran; hexane;

DOI:10.1016/j.tet.2005.06.024

upstream raw materials:

6-bromo-1,4-dioxaspiro[4,5]dec-6-ene

(1R)-[1'(S)-(dibenzylamino)ethyl]oxirane

Downstream raw materials:

2-[(2R,3S)-2-acetoxy-3-dibenzylaminobutyl]cyclohex-2-enone

2-[(2R,3S)-2-acetoxy-3-(dibenzylamino)butyl]-1-butylcyclohex-2-en-1-ol

2-[(2R,3S)-2-acetoxy-3-(dibenzylamino)butyl]-3-butylcyclohex-2-enone