(S)-1-((2S,6S)-6-(3-(2-methyl-1,3-dioxolan-2-yl)propyl)piperidin-2-yl)pentan-2-ol

Base Information

• Chemical Name: (S)-1-((2S,6S)-6-(3-(2-methyl-1,3-dioxolan-2-yl)propyl)piperidin-2-yl)pentan-2-ol
• CAS No.: 888745-54-8
• Molecular Formula: C₁₇H₃₃NO₃
• Molecular Weight: 299.454
• Mol file: 888745-54-8.mol

Synonyms:

Chemical Property of (S)-1-((2S,6S)-6-(3-(2-methyl-1,3-dioxolan-2-yl)propyl)piperidin-2-yl)pentan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-((2S,6S)-6-(3-(2-methyl-1,3-dioxolan-2-yl)propyl)piperidin-2-yl)pentan-2-ol

There total 20 articles about (S)-1-((2S,6S)-6-(3-(2-methyl-1,3-dioxolan-2-yl)propyl)piperidin-2-yl)pentan-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: 85.0%

(3S,4aS,8S)-hexahydro-8-(3-(2-methyl-1,3-dioxolan-2-yl)propyl)-3-propylpyrido[1,2-c][1,3]oxazin-1(3H)-one (888745-50-4) → (S)-1-((2S,6S)-6-(3-(2-methyl-1,3-dioxolan-2-yl)propyl)piperidin-2-yl)pentan-2-ol (888745-54-8)

Guidance literature:

With potassium hydroxide; In isopropyl alcohol; at 120 ℃; for 72h;

DOI:10.1039/b601489e

Reference yield:

C25H32O6S2 → (S)-1-((2S,6S)-6-(3-(2-methyl-1,3-dioxolan-2-yl)propyl)piperidin-2-yl)pentan-2-ol (888745-54-8)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 61 percent / 48 h / 75 °C

2.1: 93 percent / CHCl₃ / 48 h / 90 °C

3.1: 32 percent / AD-mix-α / 2-methyl-propan-2-ol; H2O / 9 h / 0 °C

4.1: Et₃N; n-Bu₂SnO / CH₂Cl₂ / 1.5 h / 20 °C

5.1: 125 mg / K₂CO₃ / methanol / 1 h / 20 °C

6.1: CuBr*Me₂S / tetrahydrofuran / 1 h / -45 °C

6.2: 76 percent / tetrahydrofuran / 1 h / -30 °C

7.1: 90 percent / (i-Pr)2NEt / CHCl₃ / Heating

8.1: aq. OsO₄ / dioxane / 0.17 h / 20 °C

8.2: NaIO₄ / dioxane; H₂O / 1.25 h / 20 °C

9.1: NaH / tetrahydrofuran / 0.08 h / 20 °C

9.2: 85 percent / tetrahydrofuran / 0 °C

10.1: 99 percent / H₂ / Pd(OH)2 / ethyl acetate / 2 h

11.1: 50 percent / TMSI / acetonitrile / 2 h / 0 °C

12.1: 92 percent / p-TsOH*H₂O / benzene / Heating

13.1: 85 percent / KOH / propan-2-ol / 72 h / 120 °C

With potassium hydroxide; AD-mix-α; osmium(VIII) oxide; copper(I) bromide dimethylsulfide complex; trimethylsilyl iodide; hydrogen; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; water; ethyl acetate; isopropyl alcohol; acetonitrile; tert-butyl alcohol; benzene; 3.1: Sharpless asymmetric dihydroxylation / 9.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1039/b601489e

Reference yield:

4,8-dihydroxy-1,10-undecanediene (111512-38-0) → (S)-1-((2S,6S)-6-(3-(2-methyl-1,3-dioxolan-2-yl)propyl)piperidin-2-yl)pentan-2-ol (888745-54-8)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 78 percent / Et₃N; 4-dimethylaminopyridine / 48 h / 20 °C

2.1: 61 percent / 48 h / 75 °C

3.1: 93 percent / CHCl₃ / 48 h / 90 °C

4.1: 32 percent / AD-mix-α / 2-methyl-propan-2-ol; H2O / 9 h / 0 °C

5.1: Et₃N; n-Bu₂SnO / CH₂Cl₂ / 1.5 h / 20 °C

6.1: 125 mg / K₂CO₃ / methanol / 1 h / 20 °C

7.1: CuBr*Me₂S / tetrahydrofuran / 1 h / -45 °C

7.2: 76 percent / tetrahydrofuran / 1 h / -30 °C

8.1: 90 percent / (i-Pr)2NEt / CHCl₃ / Heating

9.1: aq. OsO₄ / dioxane / 0.17 h / 20 °C

9.2: NaIO₄ / dioxane; H₂O / 1.25 h / 20 °C

10.1: NaH / tetrahydrofuran / 0.08 h / 20 °C

10.2: 85 percent / tetrahydrofuran / 0 °C

11.1: 99 percent / H₂ / Pd(OH)2 / ethyl acetate / 2 h

12.1: 50 percent / TMSI / acetonitrile / 2 h / 0 °C

13.1: 92 percent / p-TsOH*H₂O / benzene / Heating

14.1: 85 percent / KOH / propan-2-ol / 72 h / 120 °C

With dmap; potassium hydroxide; AD-mix-α; osmium(VIII) oxide; copper(I) bromide dimethylsulfide complex; trimethylsilyl iodide; hydrogen; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; water; ethyl acetate; isopropyl alcohol; acetonitrile; tert-butyl alcohol; benzene; 4.1: Sharpless asymmetric dihydroxylation / 10.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1039/b601489e

upstream raw materials:

(3S,4aS,8S)-hexahydro-8-(3-(2-methyl-1,3-dioxolan-2-yl)propyl)-3-propylpyrido[1,2-c][1,3]oxazin-1(3H)-one

(2S,6S)-methyl 2-allyl-6-((R)-2-(methoxymethoxy)pentyl)-piperidinecarboxylate

C₁₉H₃₃NO₅

(2S,6S)-methyl 2-((R)-2-(methoxymethoxy)pentyl)-6-(4-oxopentyl)piperidine-1-carboxylate