(-)-Nupharolutine

Base Information

• Chemical Name: (-)-Nupharolutine
• CAS No.: 38681-18-4
• Molecular Formula: C15H23NO2
• Molecular Weight: 249.34862
• Mol file: 38681-18-4.mol

Synonyms:

Chemical Property of (-)-Nupharolutine

Chemical Property:

• Melting Point: 96-8°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Also present in the rhizomes of Nuphar luteurn, this alkaloid forms colourless crystals when purified by recrystallization from MeOH-Me2CO. The base is laevorotatory with [α] 22 D- 105° (CHC13).

Technology Process of (-)-Nupharolutine

There total 17 articles about (-)-Nupharolutine 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: 40.0%

C22H29N3O4S (77647-87-1) → (+/-)-nupharolutine (38681-18-4,40766-93-6,73789-08-9,73789-09-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; a) RT, 3 h, b) reflux, 3 h;

Reference yield: 26.0%

4-(furan-3-yl)-1-methyl-7-methyleneoctahydro-2H-quinolizine (60161-30-0) → nupharolutine (38681-18-4) + (–)-castoramine (6874-86-8)

Guidance literature:

4-(furan-3-yl)-1-methyl-7-methyleneoctahydro-2H-quinolizine; With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 20 ℃; for 1h;

DOI:10.1021/jo048455k

Reference yield:

2(S)-[N-(p-toluenesulfonyl)-aziridin-2(S)-yl]-propan-1-ol (616866-42-3) → nupharolutine (38681-18-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 0.61 g / imidazole / tetrahydrofuran / 5 h

2.1: n-butyllithium; TMEDA / diethyl ether / 16 h / 0 - 20 °C

2.2: MgBr₂ / diethyl ether / 0 °C

2.3: 92 percent / diethyl ether; tetrahydrofuran / 16 h / 20 °C

3.1: 87 percent / ADDP; tributylphosphine / toluene / 16 h / 20 °C

4.1: 86 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

5.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 20 °C

6.1: 256 mg / tetrahydrofuran / 16 h / 20 °C

7.1: 72 percent / magnesium; methanol / 3 h / 20 °C

8.1: BuLi / diethyl ether / 0.33 h / -78 °C

8.2: diethyl ether / 1.5 h / -78 - 20 °C

8.3: 76 percent / diisobutylaluminum hydride / diethyl ether; CH₂Cl₂ / 1 h

9.1: borane-dimethyl sulfide / tetrahydrofuran / 1 h / 0 - 20 °C

9.2: 26 percent / hydrogen peroxide; NaOH / tetrahydrofuran; H₂O / 1 h / 20 °C

With 1H-imidazole; methanol; n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; tributylphosphine; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; magnesium; dimethyl sulfoxide; triethylamine; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 3.1: Mitsunobu reaction / 5.1: Swern oxidation / 6.1: Wittig reaction;

DOI:10.1021/jo048455k

upstream raw materials:

4-(furan-3-yl)-1-methyl-7-methyleneoctahydro-2H-quinolizine

(1R,9S)-1-methyl-7-methyleneoctahydro-4H-quinolizin-4-one

2(S)-[N-(p-toluenesulfonyl)-aziridin-2(S)-yl]-propan-1-ol

(1R,2S)-N-(3-hydroxy-1-hydroxymethyl-2-methyl-propyl)-4-methylbenzenesulfonamide

Refernces

• 1、 Natsume, Mitsutaka,Ogawa, Masashi. "A FACILE SYNTHESIS OF A NUPHAR ALKALOID, NUPHAROLUTINE". . p. 237 - 240. Retrieved 2007/10/02.