2-((4aS,6R,8aR)-5-Benzyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridin-6-yl)-ethanol

Base Information

• Chemical Name: 2-((4aS,6R,8aR)-5-Benzyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridin-6-yl)-ethanol
• CAS No.: 179536-73-3
• Molecular Formula: C₁₈H₂₇NO₃
• Molecular Weight: 305.417
• Mol file: 179536-73-3.mol

Synonyms:2-((4aS,6R,8aR)-5-Benzyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridin-6-yl)-ethanol

Chemical Property of 2-((4aS,6R,8aR)-5-Benzyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridin-6-yl)-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((4aS,6R,8aR)-5-Benzyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridin-6-yl)-ethanol

There total 13 articles about 2-((4aS,6R,8aR)-5-Benzyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridin-6-yl)-ethanol 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:

ethyl 1-benzyl-3,6-dioxo-2-piperidinecarboxylate (92912-21-5) → 2-((4aS,6R,8aR)-5-Benzyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridin-6-yl)-ethanol (179536-73-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 88 percent / baker's yeast / H₂O

2: 98 percent / Huenig base / CHCl₃ / Heating

3: 96 percent / Super-Hydride / tetrahydrofuran / 0 °C

4: 96 percent / NaH / dimethylformamide; benzene

5: conc. HCl / methanol / Heating

6: PCC, AcONa / CH₂Cl₂

7: 1.) H₂, 2.) NaB(OAc)3H / 1.) Pd(OH)2 / 1.) MeOH, 2.) AcOH

8: 88 percent / pyridine

9: 99 percent / Lawesson's reagent / tetrahydrofuran / Heating

10: 92 percent / PPh₃, Et₃N / acetonitrile / Heating

11: 84 percent / NaBH₃CN, TFA / CH₂Cl₂ / 0 °C

12: 84 percent / LiAlH₄ / tetrahydrofuran / Heating

13: p-TsOH, MS 5A / CH₂Cl₂ / Ambient temperature

With Lawessons reagent; pyridine; hydrogenchloride; lithium aluminium tetrahydride; baker's yeast; hydrogen; sodium acetate; sodium tris(acetoxy)borohydride; sodium hydride; lithium triethylborohydride; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo990397t

Reference yield:

(2R,3S)-1-Benzyl-3-hydroxy-6-oxo-piperidine-2-carboxylic acid ethyl ester (165672-46-8) → 2-((4aS,6R,8aR)-5-Benzyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridin-6-yl)-ethanol (179536-73-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 98 percent / Huenig base / CHCl₃ / Heating

2: 96 percent / Super-Hydride / tetrahydrofuran / 0 °C

3: 96 percent / NaH / dimethylformamide; benzene

4: conc. HCl / methanol / Heating

5: PCC, AcONa / CH₂Cl₂

6: 1.) H₂, 2.) NaB(OAc)3H / 1.) Pd(OH)2 / 1.) MeOH, 2.) AcOH

7: 88 percent / pyridine

8: 99 percent / Lawesson's reagent / tetrahydrofuran / Heating

9: 92 percent / PPh₃, Et₃N / acetonitrile / Heating

10: 84 percent / NaBH₃CN, TFA / CH₂Cl₂ / 0 °C

11: 84 percent / LiAlH₄ / tetrahydrofuran / Heating

12: p-TsOH, MS 5A / CH₂Cl₂ / Ambient temperature

With Lawessons reagent; pyridine; hydrogenchloride; lithium aluminium tetrahydride; hydrogen; sodium acetate; sodium tris(acetoxy)borohydride; sodium hydride; lithium triethylborohydride; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo990397t

Reference yield:

(5S,6S)-1-Benzyl-6-hydroxymethyl-5-methoxymethoxy-piperidin-2-one (165672-49-1) → 2-((4aS,6R,8aR)-5-Benzyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridin-6-yl)-ethanol (179536-73-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 96 percent / NaH / dimethylformamide; benzene

2: conc. HCl / methanol / Heating

3: PCC, AcONa / CH₂Cl₂

4: 1.) H₂, 2.) NaB(OAc)3H / 1.) Pd(OH)2 / 1.) MeOH, 2.) AcOH

5: 88 percent / pyridine

6: 99 percent / Lawesson's reagent / tetrahydrofuran / Heating

7: 92 percent / PPh₃, Et₃N / acetonitrile / Heating

8: 84 percent / NaBH₃CN, TFA / CH₂Cl₂ / 0 °C

9: 84 percent / LiAlH₄ / tetrahydrofuran / Heating

10: p-TsOH, MS 5A / CH₂Cl₂ / Ambient temperature

With Lawessons reagent; pyridine; hydrogenchloride; lithium aluminium tetrahydride; hydrogen; sodium acetate; sodium tris(acetoxy)borohydride; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo990397t

upstream raw materials:

2,2-dimethoxy-propane

[(5R,6S)-5-Acetoxy-6-acetoxymethyl-1-benzyl-piperidin-(2E)-ylidene]-acetic acid methyl ester

ethyl 1-benzyl-3,6-dioxo-2-piperidinecarboxylate

(5R,6S)-1-Benzyl-5-hydroxy-6-hydroxymethyl-piperidin-2-one

Downstream raw materials:

(4aS,6R,8aR)-5-Benzyl-6-[(Z)-9-(2-ethyl-[1,3]dioxolan-2-yl)-non-2-enyl]-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine

(3R,4S,6S,9aS)-(-)-{[(2,2-dimethyl)diphenylsiloxy]methyl}-3-(methoxymethoxy)-6-(phenylsulfonylmethyl)octahydro-2H-quinolizine

(3R,4S,6S,9aS)-(-)-4-{[(2,2-dimethylethyl)diphenylsiloxy]methyl}-3-hydroxy-6-(phenylsulfonylmethyl)-octahydro-2H-quinolizine

(4aS,5S,8aS,10aR)-5-Benzenesulfonylmethyl-2,2-dimethyl-decahydro-1,3-dioxa-4b-aza-phenanthrene