2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-ol

Base Information

• Chemical Name: 2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-ol
• CAS No.: 145307-22-8
• Molecular Formula: C11H21 N O
• Molecular Weight: 183.294
• Mol file: 145307-22-8.mol

Synonyms:1H-2-Pyrindin-6-ol,octahydro-2,4,7-trimethyl-, [4R-(4a,4ab,6b,7b,7ab)]-; (-)-Incarvilline;1H-Cyclopenta[c]pyridin-6-ol, octahydro-2,4,7-trimethyl-, [4R-(4a,4ab,6b,7b,7ab)]-; Incarvilline

Chemical Property of 2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-ol

Chemical Property:

• Vapor Pressure: 0.0023mmHg at 25°C
• Melting Point: 93.4 - 93.8 °C (cyclohexane)
• Boiling Point: 256.5°Cat760mmHg
• Flash Point: 49°C
• PSA: 23.47000
• Density: 0.971g/cm³
• LogP: 1.13890

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-ol

There total 31 articles about 2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-ol 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: 83.0%

4-Methoxy-benzoic acid (4R,4aS,6R,7S,7aR)-2,4,7-trimethyl-octahydro-[2]pyrindin-6-yl ester (851008-94-1) → (4R,4aS,6R,7S,7aR)-2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-ol (145307-22-8)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; Heating;

DOI:10.1016/j.tetlet.2005.01.173

Reference yield: 67.0%

(4R,4aS,6R,7S,7aR)-2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-yl 4-nitrobenzoate (823788-03-0) → (4R,4aS,6R,7S,7aR)-2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-ol (145307-22-8)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1021/ja0401702

Reference yield:

(4S)-4-tert-butyldimethylsilyloxycyclopent-2-en-1-one (56745-67-6,61305-35-9,61740-33-8,61305-36-0) → (4R,4aS,6R,7S,7aR)-2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-ol (145307-22-8)

Guidance literature:

Multi-step reaction with 15 steps

1.1: butyllithium; dimethylzinc / tetrahydrofuran; hexane / 0.25 h / 0 °C

1.2: tetrahydrofuran; hexane / 0.25 h / -78 °C

1.3: 77 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 16 h / -40 °C

2.1: ozone / CH₂Cl₂; methanol / -78 °C

2.2: 96 percent / methyl sulfide / CH₂Cl₂; methanol / 2 h / 20 °C

3.1: 71 percent / sodium borohydride / tetrahydrofuran; ethanol / 0.5 h

4.1: 99 percent / triphenylphosphine; diethyl azidocarboxylate / tetrahydrofuran / 1 h / 20 °C

5.1: 95 percent / trifluoroacetic acid / CH₂Cl₂ / 16 h / 20 °C

6.1: 81 percent / K₂CO₃ / acetonitrile / 3 h / Heating

7.1: 10 percent / palladium(II) acetate; N,N'-bis(benzylidene)ethylenediamine; poly(methylhydrosiloxane) / acetic acid / benzene / 4 h / 95 °C

8.1: 97 percent / sodium borohydrate / methanol / 0.5 h

9.1: 93 percent / imidazole / dimethylformamide / 16 h / 20 °C

10.1: 78 percent / sodium naphthalenide; sodium / 1,2-dimethoxy-ethane / 0.5 h / -50 °C

11.1: 97 percent / aq. NaBH₃CN / acetonitrile / 0.25 h / 20 °C

12.1: 84 percent / platinum(II) oxide; H₂ / methanol / 24 h / 3800 Torr

13.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 36 h / 20 °C

14.1: 66 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 6 h / 20 °C

15.1: 67 percent / aq. NaOH / tetrahydrofuran / 24 h / 20 °C

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; platinum(II) oxide; N,N'-bis(benzyliden)ethylendiamine; tetrabutyl ammonium fluoride; hydrogen; dimethyl zinc(II); palladium diacetate; sodium; sodium naphthalenide; sodium cyanoborohydride; potassium carbonate; ozone; triphenylphosphine; trifluoroacetic acid; poly(methylhydrosiloxane); diethylazodicarboxylate; acetic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene; 4.1: Mitsunobu reaction / 14.1: Mitsunobu reaction;

DOI:10.1021/ja0401702

upstream raw materials:

(4R,4aS,6R,7S,7aR)-2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-yl 4-nitrobenzoate

4-Methoxy-benzoic acid (4R,4aS,6R,7S,7aR)-2,4,7-trimethyl-octahydro-[2]pyrindin-6-yl ester

(4R,4aS,6S,7S,7aR)-2,4,7-trimethyl-octahydro-1H-cyclopenta[c]pyridin-6-ol

(4R,4aS,6S,7S,7aR)-4,7-Dimethyl-octahydro-[2]pyrindin-6-ol

Downstream raw materials:

bis[(4R,4aS,6R,7S,7aR)-2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-yl] 2,4-bis(3-methoxy-4-{[(4-methylphenyl)sulfonyl]oxy}phenyl)cyclobutane-1,3-dicarboxylate

Refernces

Total synthesis of (-)-incarvilline, (+)-incarvine C, and (-)-incarvillateine

10.1021/ja0401702

The study presents the first total syntheses of the monoterpene alkaloids (-)-incarvilline, (+)-incarvine C, and (-)-incarvillateine, which are natural compounds with potent analgesic activity. The synthesis strategy utilized 6-epi-incarvilline as a common precursor, constructed through a three-component coupling reaction and a reductive Heck-type reaction to form the cyclopentanone and perhydro-2-pyrindine skeletons, respectively. Additionally, the study investigated the topochemically controlled [2 + 2] photodimerization of cinnamic acid derivatives to construct the 1,2,3,4-tetrasubstituted cyclobutane ring specific to (-)-incarvillateine. Various chemicals were employed, including (4S)-4-siloxy-2-cyclopenten-1-one, organozinc reagents, iodomethane, N-Boc-tosyl amide, and palladium catalysts, among others, to achieve the desired synthetic transformations and construct the complex molecular frameworks of the target alkaloids. These chemicals served the purpose of facilitating specific reactions and transformations necessary to synthesize the target compounds, ultimately allowing for the establishment of their structures and absolute configurations.