2-((1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((3S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalen-5-yloxy)acetonitrile

Base Information

• Chemical Name: 2-((1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((3S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalen-5-yloxy)acetonitrile
• CAS No.: 101692-03-9
• Molecular Formula: C₂₃H₃₃NO₃
• Molecular Weight: 371.52
• Mol file: 101692-03-9.mol

Synonyms:2-((1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((3S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalen-5-yloxy)acetonitrile

Chemical Property of 2-((1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((3S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalen-5-yloxy)acetonitrile

Chemical Property:

• Boiling Point: 565.7±50.0 °C(Predicted)
• Density: 1.106±0.06 g/cm3(Predicted)

Purity/Quality:

>95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Descarboxymethyl Cyanomethyl Treprostinil is used as a reactant in the stereoselective preparation of intermediates and Treprostinil. Treprostinil (T719500) is antihypertensive. Treprostinil, marketed under the trade name Remodulin is a medication used to treat pulmonary arterial hypertension (PAH).

Technology Process of 2-((1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((3S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalen-5-yloxy)acetonitrile

There total 1 articles about 2-((1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((3S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalen-5-yloxy)acetonitrile 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:

2-allyl-3-methoxybenzaldehyde (94956-98-6) → 2-((1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((3S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalen-5-yloxy)acetonitrile (101692-03-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 92 percent / EtMgBr / tetrahydrofuran; diethyl ether / 0 - 20 °C

2: 75 percent / PCC / CH₂Cl₂ / 15 h / 0 - 20 °C

3: BH₃; Me₂S; (R)-methyloxazaborolidine / toluene; tetrahydrofuran / 1 h / -30 °C

4: 92 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide; CH₂Cl₂ / 15 h / 20 °C

5: CH₂Cl₂ / 2 h / 20 °C

6: H₂; K₂CO₃ / Pd/C / ethanol / 20 °C / 4654.33 Torr

7: NaBH₄; aq. NaOH / ethanol / 6 h / -10 °C

8: 2162 g / TsOH / methanol / 15 h / 0 - 20 °C

9: 80 percent / Ph₂PH; n-BuLi / tetrahydrofuran; hexane / 20 h / Heating

10: 100 percent / K₂CO₃; tetrabutylammonium bromide / acetone / 8 h / Heating

With 1H-imidazole; dmap; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; dimethylsulfide; (R)-methyloxazaborolidine; borane; ethylmagnesium bromide; tetrabutylammomium bromide; hydrogen; potassium carbonate; toluene-4-sulfonic acid; pyridinium chlorochromate; diphenylphosphane; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 3: Corey reduction / 5: Pauson-Khand cyclization;

DOI:10.1021/jo0347720

Reference yield: 86.0%

2-((1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((3S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalen-5-yloxy)acetonitrile (101692-03-9) → treprostinil (81846-19-7)

Guidance literature:

With potassium hydroxide; In methanol; water; at 60 ℃; for 3h; Inert atmosphere;

upstream raw materials:

2-allyl-3-methoxybenzaldehyde

Downstream raw materials:

treprostinil

Refernces