1-<1-(4-toluensulphonyl)-1-azacyclopentan-2-yl>-3-hydroxy-3-phenyl-1-propanone

Base Information

• Chemical Name: 1-<1-(4-toluensulphonyl)-1-azacyclopentan-2-yl>-3-hydroxy-3-phenyl-1-propanone
• CAS No.: 77815-27-1
• Molecular Formula: C₂₀H₂₃NO₄S
• Molecular Weight: 373.473
• Mol file: 77815-27-1.mol

Synonyms:1-<1-(4-toluensulphonyl)-1-azacyclopentan-2-yl>-3-hydroxy-3-phenyl-1-propanone

Chemical Property of 1-<1-(4-toluensulphonyl)-1-azacyclopentan-2-yl>-3-hydroxy-3-phenyl-1-propanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-<1-(4-toluensulphonyl)-1-azacyclopentan-2-yl>-3-hydroxy-3-phenyl-1-propanone

There total 4 articles about 1-<1-(4-toluensulphonyl)-1-azacyclopentan-2-yl>-3-hydroxy-3-phenyl-1-propanone 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: 57.0%

(S)-(-)-<1-(4-toluensulphonyl)-1-azacyclopentan-2-yl>ethanone (77815-24-8) + benzaldehyde (100-52-7) → 1-<1-(4-toluensulphonyl)-1-azacyclopentan-2-yl>-3-hydroxy-3-phenyl-1-propanone (77815-27-1) + 1-<1-(4-toluensulphonyl)-1-azacyclopentan-2-yl>-3-hydroxy-3-phenyl-1-propanone (77815-26-0)

Guidance literature:

With oxodiperoxymolybdenumpyridine hexamethylphosphoric triamide complex; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; Product distribution; multistep reaction: 1.) Et₂O, -78 deg C, 60 min, 2.) -78 deg C, 30 min; other solvents, temperatures; aldol condensation via lithium enolates; metal-dependent aldol condensation;

DOI:10.1021/ja00401a031

Reference yield:

L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → 1-<1-(4-toluensulphonyl)-1-azacyclopentan-2-yl>-3-hydroxy-3-phenyl-1-propanone (77815-27-1)

Guidance literature:

Multi-step reaction with 3 steps

2: 50 percent / diethyl ether / 5 h / Ambient temperature

3: 19 percent / 1.) di-n-butylboryl triflate, diisopropylethylamine, 3.) MoO₅*py*HMPT / multistep reaction: 1.) Et₂O, -78 deg C, 60 min, 2.) -78 deg C, 30 min; other solvents, temperatures; aldol condensation via lithium enolates; metal-dependent aldol condensation

With oxodiperoxymolybdenumpyridine hexamethylphosphoric triamide complex; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In diethyl ether;

DOI:10.1021/ja00401a031

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → 1-<1-(4-toluensulphonyl)-1-azacyclopentan-2-yl>-3-hydroxy-3-phenyl-1-propanone (77815-27-1)

Guidance literature:

Multi-step reaction with 3 steps

2: 50 percent / diethyl ether / 5 h / Ambient temperature

3: 19 percent / 1.) di-n-butylboryl triflate, diisopropylethylamine, 3.) MoO₅*py*HMPT / multistep reaction: 1.) Et₂O, -78 deg C, 60 min, 2.) -78 deg C, 30 min; other solvents, temperatures; aldol condensation via lithium enolates; metal-dependent aldol condensation

With oxodiperoxymolybdenumpyridine hexamethylphosphoric triamide complex; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In diethyl ether;

DOI:10.1021/ja00401a031

upstream raw materials:

(S)-(-)-<1-(4-toluensulphonyl)-1-azacyclopentan-2-yl>ethanone

benzaldehyde

L-proline

p-toluenesulfonyl chloride

Downstream raw materials:

(S)-3-hydroxy-3-phenylpropanoic acid