(2R,3S)-1-Methyl-2-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylmethyl]-piperidine-3-carboxylic acid

Base Information

• Chemical Name: (2R,3S)-1-Methyl-2-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylmethyl]-piperidine-3-carboxylic acid
• CAS No.: 761435-63-6
• Molecular Formula: C₂₅H₂₈N₂O₅S
• Molecular Weight: 468.574
• Mol file: 761435-63-6.mol

Synonyms:(2R,3S)-1-Methyl-2-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylmethyl]-piperidine-3-carboxylic acid

Chemical Property of (2R,3S)-1-Methyl-2-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylmethyl]-piperidine-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-1-Methyl-2-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylmethyl]-piperidine-3-carboxylic acid

There total 6 articles about (2R,3S)-1-Methyl-2-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylmethyl]-piperidine-3-carboxylic acid 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: 100.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (2R,3S)-2-[4-(2-Methyl-quinolin-4-ylmethoxy)-benzenesulfonylmethyl]-piperidine-3-carboxylic acid (761435-61-4) → (2R,3S)-1-Methyl-2-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylmethyl]-piperidine-3-carboxylic acid (761435-63-6)

Guidance literature:

With 4-methyl-morpholine; sodium tris(acetoxy)borohydride; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2004.06.049

Reference yield:

(S)-2-[(R)-1-Benzyloxycarbonylamino-2-(4-benzyloxy-phenylsulfanyl)-ethyl]-pent-4-enoic acid tert-butyl ester (761435-49-8) → (2R,3S)-1-Methyl-2-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylmethyl]-piperidine-3-carboxylic acid (761435-63-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / Oxone / methanol; H₂O

2: 67 percent / 9-BBN / tetrahydrofuran

3: 71 percent / pyridinium dichromate / CH₂Cl₂

4: 95 percent / H₂ / Pd-C / methanol

5: 90 percent / tetrahydrofuran; H₂O

6: 65 percent / K₂CO₃ / dimethylformamide

7: 100 percent / TFA / CH₂Cl₂

8: 100 percent / Na(OAc)3BH; NMM / tetrahydrofuran

With 4-methyl-morpholine; Oxone; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; hydrogen; sodium tris(acetoxy)borohydride; potassium carbonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.06.049

Reference yield:

(S)-2-[(R)-2-(4-Benzyloxy-benzenesulfonyl)-1-benzyloxycarbonylamino-ethyl]-5-oxo-pentanoic acid tert-butyl ester (761435-55-6) → (2R,3S)-1-Methyl-2-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylmethyl]-piperidine-3-carboxylic acid (761435-63-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / H₂ / Pd-C / methanol

2: 90 percent / tetrahydrofuran; H₂O

3: 65 percent / K₂CO₃ / dimethylformamide

4: 100 percent / TFA / CH₂Cl₂

5: 100 percent / Na(OAc)3BH; NMM / tetrahydrofuran

With 4-methyl-morpholine; hydrogen; sodium tris(acetoxy)borohydride; potassium carbonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.06.049

upstream raw materials:

formaldehyd

(2R,3S)-2-[4-(2-Methyl-quinolin-4-ylmethoxy)-benzenesulfonylmethyl]-piperidine-3-carboxylic acid

(2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-piperidine-3-carboxylic acid tert-butyl ester

(2R,3S)-2-(4-Hydroxy-benzenesulfonylmethyl)-piperidine-1,3-dicarboxylic acid di-tert-butyl ester