2-Desoxy-4-epi-pulchellin

Base Information

• Chemical Name: 2-Desoxy-4-epi-pulchellin
• CAS No.: 122872-03-1
• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.338
• Mol file: 122872-03-1.mol

Synonyms:Saphris;Saphris,Asenapine maleate;Sycrest;trans-5-Chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenz<2,3:6,7>oxepino<4,5-c>pyrrolidine maleate;

Chemical Property of 2-Desoxy-4-epi-pulchellin

Chemical Property:

• PSA: 46.53000
• LogP: 2.29130

Purity/Quality:

≥98% ^*data from raw suppliers

2-Desoxy-4-epi-pulchellin ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Desoxy-4-epi-pulchellin

There total 25 articles about 2-Desoxy-4-epi-pulchellin 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:

(1SR,2SR,7SR,8SR)-2,7-dimethyl-8-hydroxybicyclo<5.3.0>decan-4-one (80801-05-4) → <3aRS,4aSR,5SR,7aSR,8SR,9aRS>-5-Hydroxy-4a,8-dimethyl-3-methylen-decahydroazuleno<6,5-b>furan-2(3H)-on (60403-33-0,68832-40-6,76189-79-2,114579-31-6,122872-03-1,146726-71-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / pyridine / CH₂Cl₂ / 2 h

2: 1.) LDA / 1.) DME, hexane, 60 min, 2.) 2 h

3: 100 percent / KOH / methanol / 3 h / Ambient temperature

4: 1.) 70percent HClO₄, 2.) H₂ / 2.) rhodium on alumina / 1.) EtOAc, 0 deg C, 75 min, 2.) 60 psi, 6 h

5: 80 percent / KOH / methanol; H₂O / 18 h / 0 °C

6: 1.) LDA / 1.) DNE, pentane, -68 deg C, 2 h, 2.) 45 min

7: 1.) MeI, 2.) NaHCO₃ / 1.) MeOH, 18 h, 2.) EtOAc, H₂O

With pyridine; potassium hydroxide; perchloric acid; hydrogen; sodium hydrogencarbonate; lithium diisopropyl amide; methyl iodide; Rh/Al₂O₃; In methanol; dichloromethane; water;

DOI:10.1021/ja00371a020

Reference yield:

(1SR,7SR,8SR)-2,7-dimethyl-8-hydroxybicyclo<5.3.0>dec-2-en-4-one (80800-97-1) → <3aRS,4aSR,5SR,7aSR,8SR,9aRS>-5-Hydroxy-4a,8-dimethyl-3-methylen-decahydroazuleno<6,5-b>furan-2(3H)-on (60403-33-0,68832-40-6,76189-79-2,114579-31-6,122872-03-1,146726-71-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 83 percent / H₂ / 5percent Rh on alumina / ethanol

2: 100 percent / pyridine / CH₂Cl₂ / 2 h

3: 1.) LDA / 1.) DME, hexane, 60 min, 2.) 2 h

4: 100 percent / KOH / methanol / 3 h / Ambient temperature

5: 1.) 70percent HClO₄, 2.) H₂ / 2.) rhodium on alumina / 1.) EtOAc, 0 deg C, 75 min, 2.) 60 psi, 6 h

6: 80 percent / KOH / methanol; H₂O / 18 h / 0 °C

7: 1.) LDA / 1.) DNE, pentane, -68 deg C, 2 h, 2.) 45 min

8: 1.) MeI, 2.) NaHCO₃ / 1.) MeOH, 18 h, 2.) EtOAc, H₂O

With pyridine; potassium hydroxide; perchloric acid; hydrogen; sodium hydrogencarbonate; lithium diisopropyl amide; methyl iodide; Rh/Al₂O₃; rhodium on alumina; In methanol; ethanol; dichloromethane; water;

DOI:10.1021/ja00371a020

Reference yield:

C15H22O5 (80844-98-0) → <3aRS,4aSR,5SR,7aSR,8SR,9aRS>-5-Hydroxy-4a,8-dimethyl-3-methylen-decahydroazuleno<6,5-b>furan-2(3H)-on (60403-33-0,68832-40-6,76189-79-2,114579-31-6,122872-03-1,146726-71-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 2.) AcOH, NaOAc / 1.) THF, 0 deg C, 1 h, 2.) H₂O, steam bath, 30 min

2: 83 percent / H₂ / 5percent Rh on alumina / ethanol

3: 100 percent / pyridine / CH₂Cl₂ / 2 h

4: 1.) LDA / 1.) DME, hexane, 60 min, 2.) 2 h

5: 100 percent / KOH / methanol / 3 h / Ambient temperature

6: 1.) 70percent HClO₄, 2.) H₂ / 2.) rhodium on alumina / 1.) EtOAc, 0 deg C, 75 min, 2.) 60 psi, 6 h

7: 80 percent / KOH / methanol; H₂O / 18 h / 0 °C

8: 1.) LDA / 1.) DNE, pentane, -68 deg C, 2 h, 2.) 45 min

9: 1.) MeI, 2.) NaHCO₃ / 1.) MeOH, 18 h, 2.) EtOAc, H₂O

With pyridine; potassium hydroxide; perchloric acid; hydrogen; sodium acetate; sodium hydrogencarbonate; acetic acid; lithium diisopropyl amide; methyl iodide; Rh/Al₂O₃; rhodium on alumina; In methanol; ethanol; dichloromethane; water;

DOI:10.1021/ja00371a020

upstream raw materials:

N,N-dimethyl(methylene)ammonium chloride

3aα,4,4a,5,6,7,7aα,8,9,9aα-decahydro-5β-hydroxy-4aβ,8β-dimethylazuleno<6,5-b>furan-2(3)H-one

(3aS,4aR,5R,7aR,8R,9aS)-3-Dimethylaminomethyl-5-hydroxy-4a,8-dimethyl-decahydro-azuleno[6,5-b]furan-2-one

(3aS,4aR,5R,7aR,8R,9aS)-5-Hydroxy-4a,8-dimethyl-2-oxo-dodecahydro-azuleno[6,5-b]furan-3-carboxylic acid

Downstream raw materials:

(+/-)-confertin

Refernces

• 1、 Heathcock,DelMar,Graham. "Synthesis of sesquiterpene antitumor lactones. 9. The hydronaphthalene route to pseudoguaianes. Total synthesis of (±)-confertin". . p. 1907 - 1917. Retrieved 2007/10/22.