Didesmethylsibutramine, (+)-

Base Information

• Chemical Name: Didesmethylsibutramine, (+)-
• CAS No.: 229639-56-9
• Molecular Formula: C₁₅H₂₂ClN
• Molecular Weight: 251.799
• UNII: B408000HRV
• DSSTox Substance ID: DTXSID90177513
• Nikkaji Number: J1.352.498J
• Wikidata: Q7389750
• Mol file: 229639-56-9.mol

Synonyms:BTS 54 505;BTS 54505;BTS-54 505;BTS-54505

Chemical Property of Didesmethylsibutramine, (+)-

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 337.9±25.0 °C(Predicted)
• PKA: 10.82±0.42(Predicted)
• Density: 1.072±0.06 g/cm3(Predicted)
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 251.1440774
• Heavy Atom Count: 17
• Complexity: 239

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)CC(C1(CCC1)C2=CC=C(C=C2)Cl)N
• Isomeric SMILES: CC(C)C[C@H](C1(CCC1)C2=CC=C(C=C2)Cl)N

Technology Process of Didesmethylsibutramine, (+)-

There total 29 articles about Didesmethylsibutramine, (+)- 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: 95.0%

C32H39ClN2O4S2 → (R)-N-{1-[1-(4-Chlorophenyl)cyclobutyl]-3-methylbutyl}amine (229639-56-9,84467-54-9) + (S)-(-)-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine (229639-57-0,84467-54-9)

Guidance literature:

C₃₂H₃₉ClN₂O₄S₂; With sodium tetrahydroborate; titanium(IV) tetraethanolate; In tetrahydrofuran; at -15 ℃;

With hydrogenchloride; In tetrahydrofuran; methanol;

With sodium hydroxide; In tetrahydrofuran; methanol; Product distribution / selectivity;

Reference yield: 89.5%

(2S,4R,5S)-N-tosyl-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide (473554-13-1) + 1-(4-chlorophenyl)cyclobutanecarbonitrile (28049-61-8) → N-[(1R,2S)-2-hydroxy-1-methyl-2-phenylethyl]-4-methylbenzenesulfonamide (58107-41-8,58107-43-0,108591-33-9,131142-88-6,143957-01-1,136173-99-4) + (R)-N-{1-[1-(4-Chlorophenyl)cyclobutyl]-3-methylbutyl}amine (229639-56-9,84467-54-9)

Guidance literature:

With hydrogenchloride; titanium(IV) tetraethanolate; sodium hydroxide; sodium tetrahydroborate; 2-methylpropylmagnesium chloride; ammonium acetate; water; copper(I) bromide; In tetrahydrofuran; methanol; tert-butyl methyl ether; toluene; at -78 - 20 ℃; for 18 - 20h; Heating / reflux;

Reference yield: 88.0%

(R)-{1-[1-(4-chloro-phenyl)-cyclobutyl]-3-methyl-butylidene}-sulfinamic acid (1S,2R)-1-phenyl-2-(4-methylphenylsulfonylamino)-propyl ester → (R)-N-{1-[1-(4-Chlorophenyl)cyclobutyl]-3-methylbutyl}amine (229639-56-9,84467-54-9) + (S)-(-)-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine (229639-57-0,84467-54-9)

Guidance literature:

(R)-{1-[1-(4-chloro-phenyl)-cyclobutyl]-3-methyl-butylidene}-sulfinamic acid (1S,2R)-1-phenyl-2-(4-methylphenylsulfonylamino)-propyl ester; With sodium tetrahydroborate; titanium(IV) isopropylate; In tetrahydrofuran; at -45 - -30 ℃;

With hydrogenchloride; In tetrahydrofuran; methanol;

With sodium hydroxide; In tetrahydrofuran; methanol; Product distribution / selectivity;

upstream raw materials:

(2-methylpropyl)lithium

(R)-N-(1-(4-chlorophenyl)cyclobutanemethylene)-t-butanesulfinamide

1-[1-(4-chloro-phenyl)-cyclobutyl]-3-methyl-butylideneamine

1-(4-chlorophenyl)cyclobutanecarbonitrile

Downstream raw materials:

(R)-(+)-N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-N,N-dimethylamine

(R)-DDMS-D-TA

Refernces

• 1、 -. "PHENYLCYCLOBUTYLAMIDE DERIVATIVES AND THEIR STEREOISOMERS, THE PREPARATION PROCESSES AND USES THEREOF". Page/Page column 6. . Retrieved 2011/10/04.
• 2、 -. "PHENYLCYCLOBUTYLAMIDE DERIVATIVES AND THEIR STEREOISOMERS, THE PREPARING PROCESSES AND THE USES THEREOF". Page/Page column 8. . Retrieved 2010/12/30.