2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester

Base Information

• Chemical Name: 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester
• CAS No.: 81845-98-9
• Molecular Formula: C₂₄H₃₆O₅
• Molecular Weight: 404.547
• Mol file: 81845-98-9.mol

Synonyms:2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester

Chemical Property of 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester

Chemical Property:

• Boiling Point: 558.3±50.0 °C(Predicted)
• Density: 1.116±0.06 g/cm3(Predicted)

Purity/Quality:

>95% ^*data from raw suppliers

TreprostinilDiethanolamine(RS) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Treprostinil Diethanolamine (RS) is an impurity of Treprostinil (T719500) which is a synthetic analog of Prostacyclin (P839060). Antihypertensive. Treprostinil (T719500), marketed under the trade name Remodulin is a medication used to treat pulmonary arterial hypertension (PAH).

Technology Process of 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester

There total 23 articles about 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester 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: 74.8%

bromoacetic acid methyl ester (96-32-2) + (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalene-2,5-diol (101692-02-8) → 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester (81845-98-9)

Guidance literature:

With potassium carbonate; In acetone; at 50 - 60 ℃;

Reference yield:

methanol (67-56-1) + treprostinil (81846-19-7) → 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester (81845-98-9)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 24h; Time;

Reference yield:

3-allyloxy-benzaldehyde (40359-32-8) → 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester (81845-98-9)

Guidance literature:

Multi-step reaction with 11 steps

1: decalin / 7 h / 217 °C / Inert atmosphere

2: potassium carbonate; sodium iodide / acetone / 4 h / Reflux

3: n-butyllithium / hexane; tetrahydrofuran / Cooling

4: pyridinium chlorochromate / dichloromethane / 20 °C

5: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene; tetrahydrofuran / -30 - -25 °C

6: 1H-imidazole / dichloromethane / 20 °C

7: dichloromethane / 20 °C / Inert atmosphere

8: potassium carbonate; hydrogen / palladium 10% on activated carbon / ethanol / 20 °C

9: sodium hydroxide; water; sodium tetrahydroborate / ethanol

10: hydrogen / palladium 10% on activated carbon / acetic acid

11: potassium carbonate / acetone / 6.5 h / Reflux

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; dimethylsulfide borane complex; water; hydrogen; potassium carbonate; pyridinium chlorochromate; sodium iodide; sodium hydroxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; palladium 10% on activated carbon; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetic acid; acetone; toluene; decalin; 1: Claisen Rearrangement / 7: Pauson-Khand Reaction;

upstream raw materials:

3-allyloxy-benzaldehyde

bromoacetic acid methyl ester

(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalene-2,5-diol

meta-hydroxybenzaldehyde

Downstream raw materials:

treprostinil

Refernces

• 1、 -. "Process for Preparing Treprostinil and Intermediate Therefor". Paragraph 0192-0194. . Retrieved 2018/02/21.
• 2、 -. "Synthesis Of Treprostinil And Intermediates Useful Therein". . . Retrieved 2014/01/08.