(3S)-3β-Methyl-4α-[(E)-2-[(2S)-6β-methyl-2α-piperidinyl]vinyl]-1,3,3aβ,4,4aα,5,6,7,8,8aβ,9,9aβ-dodecahydronaphtho[2,3-c]furan-1-one

Base Information

• Chemical Name: (3S)-3β-Methyl-4α-[(E)-2-[(2S)-6β-methyl-2α-piperidinyl]vinyl]-1,3,3aβ,4,4aα,5,6,7,8,8aβ,9,9aβ-dodecahydronaphtho[2,3-c]furan-1-one
• CAS No.: 518-99-0
• Molecular Formula: C21H33NO2
• Molecular Weight: 331.49
• Mol file: 518-99-0.mol

Synonyms:(3S,3aR,4R,4aS,8aR,9aS)-3-Methyl-4-[(E)-2-((2R,6S)-6-methyl-piperidin-2-yl)-vinyl]-decahydro-naphtho[2,3-c]furan-1-one;himbeline;

Chemical Property of (3S)-3β-Methyl-4α-[(E)-2-[(2S)-6β-methyl-2α-piperidinyl]vinyl]-1,3,3aβ,4,4aα,5,6,7,8,8aβ,9,9aβ-dodecahydronaphtho[2,3-c]furan-1-one

Chemical Property:

• PSA: 38.33000
• LogP: 4.40600

Purity/Quality:

98%min ^*data from raw suppliers

Himbeline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Himbeline is used in the enantioselective total synthesis of (+)-himbacine and (+)-himbeline from (S)-2-methylpiperidine L-tartrate.

Technology Process of (3S)-3β-Methyl-4α-[(E)-2-[(2S)-6β-methyl-2α-piperidinyl]vinyl]-1,3,3aβ,4,4aα,5,6,7,8,8aβ,9,9aβ-dodecahydronaphtho[2,3-c]furan-1-one

There total 55 articles about (3S)-3β-Methyl-4α-[(E)-2-[(2S)-6β-methyl-2α-piperidinyl]vinyl]-1,3,3aβ,4,4aα,5,6,7,8,8aβ,9,9aβ-dodecahydronaphtho[2,3-c]furan-1-one 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: 100.0%

(2R,6S)-tert-butyl 2-[2-(E)-[(3S,3aR,4R,4aS,8aR,9aS)-dodecahydro-3-methyl-1-oxonaphtho[2,3-c]furan-4-yl]ethenyl]-6-methylpiperidine-1-carboxylate (168417-07-0) → himbeline (518-99-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1016/S0040-4020(02)01358-3

Reference yield:

1,1-dimethyl<(2R,6S)-2-formyl-6-methyl-1-piperidine>carboxylate (168610-13-7) → himbeline (518-99-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / 0.17 h / -78 °C

1.2: 45 percent / 1,2-dimethoxy-ethane; hexane / 1 h / -78 °C

2.1: 66 percent / Na-Hg; Na₂HPO₄ / methanol / 2.5 h / 20 °C

3.1: 100 percent / Jones reagent / acetone / 0.5 h / 20 °C

4.1: 100 percent / trifluoroacetic acid / CH₂Cl₂ / 1.5 h / 20 °C

With disodium hydrogenphosphate; n-butyllithium; jones reagent; sodium amalgam; trifluoroacetic acid; In methanol; 1,2-dimethoxyethane; hexane; dichloromethane; acetone; 1.2: Julia-Lythgoe reaction / 3.1: Jones oxidation;

DOI:10.1016/S0040-4020(02)01358-3

Reference yield:

(+)-(S)-N-tert-butoxycarbonyl-2-methylpiperidine (183903-99-3) → himbeline (518-99-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 39 percent / RuO₄; NaIO₄ / ethyl acetate; H₂O

2.1: 54 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

3.1: 50 percent / LiCl; (i-Pr)2EtN / acetonitrile / 12 h

4.1: TFA / CH₂Cl₂ / 0 - 20 °C

4.2: NaCNBH₃ / CH₂Cl₂; ethanol / 0.01 h / 20 °C

4.3: aq. NaHCO₃ / CH₂Cl₂; ethanol / 20 °C

5.1: Et₃N / CH₂Cl₂ / 14 h

6.1: 11 percent / H₂ / PtO₂ / ethanol / 12 h

7.1: 95 percent / TFA / CH₂Cl₂ / 1 h

With sodium periodate; n-butyllithium; ruthenium tetroxide; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium chloride; platinum(IV) oxide; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1016/j.tet.2005.09.050

upstream raw materials:

(2R,6S)-tert-butyl 2-[2-(E)-[(3S,3aR,4R,4aS,8aR,9aS)-dodecahydro-3-methyl-1-oxonaphtho[2,3-c]furan-4-yl]ethenyl]-6-methylpiperidine-1-carboxylate

(6-tert-butoxycarbonylamino-2-oxo-heptyl)-phosphonic acid dimethyl ester

(3S,3aR,4R,4aS,8aS)-3-Methyl-4-[(E)-2-((S)-6-methyl-piperidin-2-yl)-vinyl]-3a,4,4a,5,6,7,8,8a-octahydro-3H-naphtho[2,3-c]furan-1-one

[(6E,8E,14E)-(S)-1-Methyl-15-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-5-oxo-pentadeca-6,8,14-trienyl]-carbamic acid tert-butyl ester

Downstream raw materials:

himbacine

Refernces

• 1、 Tchabanenko, Kirill,Chesworth, Richard,Parker, Jeremy S.,Anand, Neel K.,Russell, Andrew T.,Adlington, Robert M.,Baldwin, Jack E.. "Biomimetic approach to Galbulimina type I alkaloids". . p. 11649 - 11656. Retrieved 2007/10/03.
• 2、 Takadoi, Masanori,Katoh, Tadashi,Ishiwata, Akihiro,Terashima, Shiro. "Synthetic studies of himbacine, a potent antagonist of the muscarinic M2 subtype receptor 1. Stereoselective total synthesis and antagonistic activity of enantiomeric pairs of himbacine and (2′S,6′R)-diepihimbacine, 4-epihimbacine, and novel himbacine congeners". . p. 9903 - 9923. Retrieved 2007/10/03.