1-exo-<3-(1-Fluorocyclohexyl)-3(R)-hydroxy-(E)-1-propenyl>-2-endo-hydroxy-5-oxooctahydropentalene

Base Information

• Chemical Name: 1-exo-<3-(1-Fluorocyclohexyl)-3(R)-hydroxy-(E)-1-propenyl>-2-endo-hydroxy-5-oxooctahydropentalene
• CAS No.: 117169-35-4
• Molecular Formula: C₁₇H₂₅FO₃
• Molecular Weight: 296.382
• Mol file: 117169-35-4.mol

Synonyms:

Chemical Property of 1-exo-<3-(1-Fluorocyclohexyl)-3(R)-hydroxy-(E)-1-propenyl>-2-endo-hydroxy-5-oxooctahydropentalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-exo-<3-(1-Fluorocyclohexyl)-3(R)-hydroxy-(E)-1-propenyl>-2-endo-hydroxy-5-oxooctahydropentalene

There total 18 articles about 1-exo-<3-(1-Fluorocyclohexyl)-3(R)-hydroxy-(E)-1-propenyl>-2-endo-hydroxy-5-oxooctahydropentalene 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:

C24H37FO5 (117169-34-3,117248-66-5) → 1-exo-<3-(1-Fluorocyclohexyl)-3(S)-hydroxy-(E)-1-propenyl>-2-endo-hydroxy-5-oxooctahydropentalene (117169-35-4,117248-67-6) + 1-exo-<3-(1-Fluorocyclohexyl)-3(R)-hydroxy-(E)-1-propenyl>-2-endo-hydroxy-5-oxooctahydropentalene (117169-35-4,117248-67-6)

Guidance literature:

With oxalic acid; In acetone; at 40 ℃; Yield given. Yields of byproduct given;

DOI:10.1055/s-1988-27551

Reference yield:

C24H37FO5 (117169-34-3,117248-66-5) → 1-exo-<3-(1-Fluorocyclohexyl)-3(S)-hydroxy-(E)-1-propenyl>-2-endo-hydroxy-5-oxooctahydropentalene (117169-35-4,117248-67-6) + 1-exo-<3-(1-Fluorocyclohexyl)-3(R)-hydroxy-(E)-1-propenyl>-2-endo-hydroxy-5-oxooctahydropentalene (117169-35-4,117248-67-6)

Guidance literature:

With oxalic acid; In acetone; at 40 ℃; Yield given. Yields of byproduct given;

DOI:10.1055/s-1988-27551

Reference yield:

1-oxaspiro<2,5>octane-2-carboxylic acid nitrile (36929-66-5,500899-63-8,500899-64-9) → 1-exo-<3-(1-Fluorocyclohexyl)-3(S)-hydroxy-(E)-1-propenyl>-2-endo-hydroxy-5-oxooctahydropentalene (117169-35-4,117248-67-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 86 percent / 70percent HF / CH₂Cl₂; pyridine / 1.) 0 deg C, 1 h, 2.) room temp., 1 h

2: 74 percent / NaBH₄ / propan-2-ol; H₂O / 1 h / 0 °C

3: 59 percent / Jones reagent / acetone / 0 °C

4: 79 percent / diethyl ether / 5 °C

5: 1.) BuLi / 1.) hexane, THF, -70 deg C, 15 min, 2.) -70 deg C, 1 h; room temp., 1 h

6: 1.) NaH / 1.) THF, 30 min, 2.) -40 deg C, 1 h; room temp., 1 h

7: NaBH₄ / methanol / 0.17 h / Ambient temperature

8: aq. (CO₂H)2 / acetone / 40 °C

With sodium tetrahydroborate; n-butyllithium; jones reagent; hydrogen fluoride; oxalic acid; sodium hydride; In pyridine; methanol; diethyl ether; dichloromethane; water; isopropyl alcohol; acetone;

DOI:10.1055/s-1988-27551

upstream raw materials:

C₂₄H₃₇FO₅

1-oxaspiro<2,5>octane-2-carboxylic acid nitrile

α-(1-Fluorocyclohexyl)-α-hydroxyacetonitrile

cyclohexanone

Downstream raw materials:

<(5E,Z),(13E)>-15-(1-Fluorocyclohexyl)-11α,(15R)-dihydroxy-ω-pentanor-9a-carbaprostacyclin

<(5E,Z),(13E)>-15-(1-Fluorocyclohexyl)-11α,(15S)-dihydroxy-ω-pentanor-9a-carbaprostacyclin

Refernces