(+)-(2S)-3-[(2S)-N-(p-toluenesulfonyl)piperidin-2-yl]propan-2-ol

Base Information

• Chemical Name: (+)-(2S)-3-[(2S)-N-(p-toluenesulfonyl)piperidin-2-yl]propan-2-ol
• CAS No.: 186891-49-6
• Molecular Formula: C₁₅H₂₃NO₃S
• Molecular Weight: 297.419
• Mol file: 186891-49-6.mol

Synonyms:(+)-(2S)-3-[(2S)-N-(p-toluenesulfonyl)piperidin-2-yl]propan-2-ol

Chemical Property of (+)-(2S)-3-[(2S)-N-(p-toluenesulfonyl)piperidin-2-yl]propan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2S)-3-[(2S)-N-(p-toluenesulfonyl)piperidin-2-yl]propan-2-ol

There total 26 articles about (+)-(2S)-3-[(2S)-N-(p-toluenesulfonyl)piperidin-2-yl]propan-2-ol 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: 79.0%

(2S)-3-[(SS,2S)-N-(p-toluenesulfinyl)piperidin-2-yl]propan-2-ol (507454-01-5) → (+)-(2S)-3-[(2S)-N-(p-toluenesulfonyl)piperidin-2-yl]propan-2-ol (186891-49-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1021/ol034119z

Reference yield:

4-nitro-benzoic acid 1-methyl-2-[1-(toluene-4-sulfonyl)-piperidin-2-yl]-ethyl ester (934472-54-5) → (+)-(2S)-3-[(2S)-N-(p-toluenesulfonyl)piperidin-2-yl]propan-2-ol (186891-49-6)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 12h;

DOI:10.1016/j.tetlet.2007.01.082

Reference yield:

N-(3-Bromo-propyl)-N-(4-methoxy-benzyl)-4-methyl-benzenesulfonamide → (+)-(2S)-3-[(2S)-N-(p-toluenesulfonyl)piperidin-2-yl]propan-2-ol (186891-49-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 49 percent / NaH, nBuLi

2: H₂, aq. HCl / <(R)-(BINAP)RuCl₂>2*NEt₃ / methanol / 10343 Torr

3: CAN / acetonitrile; H₂O

4: 2) Bu₃SnH, AIBN / 1) THF, 2) toluene

5: 1) Et₂BOMe, 2) NaBH₄

6: 1) SOCl₂, 2) NaIO₄ / 2) RuCl₃

7: 1) NaH, 2) conc. HCl / 1) THF, r.t., 45 min, 2) THF, EtOH, 20 min

With hydrogenchloride; sodium tetrahydroborate; sodium periodate; n-butyllithium; thionyl chloride; ammonium cerium(IV) nitrate; 2,2'-azobis(isobutyronitrile); diethyl methoxy borane; hydrogen; tri-n-butyl-tin hydride; sodium hydride; ruthenium trichloride; <(R)-(BINAP)RuCl2>2*NEt3; In methanol; water; acetonitrile;

DOI:10.1055/s-1997-699

upstream raw materials:

4-Methyl-N-[4-((4R,6S)-6-methyl-2,2-dioxo-2λ⁶-[1,3,2]dioxathian-4-yl)-butyl]-benzenesulfonamide

(2S)-3-[(S_S,2S)-N-(p-toluenesulfinyl)piperidin-2-yl]propan-2-ol

4-nitro-benzoic acid 1-methyl-2-[1-(toluene-4-sulfonyl)-piperidin-2-yl]-ethyl ester

[1-(toluene-4-sulfonyl)-piperidin-2-yl]-acetaldehyde

Downstream raw materials:

4-nitro-benzoic acid 1-methyl-2-[1-(toluene-4-sulfonyl)-piperidin-2-yl]-ethyl ester

(+)-(2R)-3-[(2S)-N-(p-toluenesulfonyl)piperidin-2-yl]propan-2-ol

(-)-benzyl (S)-2-[(S)-2-hydroxypropyl]piperidine-1-carboxylate

(-)-benzyl (S)-2-[(R)-2-hydroxypropyl]piperidine-1-carboxylate