(3R,5S,8R,8aR)-8-Benzyloxy-5-dodecyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile

Base Information

• Chemical Name: (3R,5S,8R,8aR)-8-Benzyloxy-5-dodecyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile
• CAS No.: 211861-26-6
• Molecular Formula: C₃₃H₄₆N₂O₂
• Molecular Weight: 502.74
• Mol file: 211861-26-6.mol

Synonyms:(3R,5S,8R,8aR)-8-Benzyloxy-5-dodecyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile

Chemical Property of (3R,5S,8R,8aR)-8-Benzyloxy-5-dodecyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S,8R,8aR)-8-Benzyloxy-5-dodecyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile

There total 9 articles about (3R,5S,8R,8aR)-8-Benzyloxy-5-dodecyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile 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: 96.0%

potassium cyanide (151-50-8) + (2R,4R,1'R)-2-(1'-benzyloxy-4'-oxohexadecyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester (209003-91-8) → (3R,5S,8R,8aR)-8-Benzyloxy-5-dodecyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile (211861-26-6)

Guidance literature:

With trifluoroacetic acid; In water; 1,2-dichloro-ethane; for 1.5h; Ambient temperature;

DOI:10.1016/S0040-4020(98)00508-0

Reference yield: 66.0%

1-dodecylbromide (143-15-7) + (3R,8R,8aR)-8-Benzyloxy-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile → (3R,5S,8R,8aR)-8-Benzyloxy-5-dodecyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile (211861-26-6)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 3h;

DOI:10.1016/S0040-4020(98)00508-0

Reference yield:

(2R,4R)-2-carboxy-4-phenyl-3-tert-butoxycarbonyloxazolidine (164530-42-1) → (3R,5S,8R,8aR)-8-Benzyloxy-5-dodecyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile (211861-26-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) N-methylmorpholine, isobutyl chloroformate, 2.) triethylamine / 1.) THF, -20 deg C, 0.5 h, 2.) THF, DMF, 0 deg C, 2 h

2: 6.3 g / diethyl ether / 0.5 h / 0 °C

3: 5.2 g / sodium borohydride / ethanol / 0.5 h / -78 °C

4: 93 percent / sodium hydride / dimethylformamide / 2 h / Ambient temperature

5: 1.) OsO₄, 2.) NaIO₄ / 1.) THF, water, room temperature, 10 min, 2) 0.5 h

6: 69 percent / trifluoroacetic acid / 1,2-dichloro-ethane; H₂O / 1.5 h / Ambient temperature

7: 66 percent / butyllithium / tetrahydrofuran; hexane / 3 h / -78 °C

With 4-methyl-morpholine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; n-butyllithium; sodium hydride; triethylamine; trifluoroacetic acid; isobutyl chloroformate; In tetrahydrofuran; diethyl ether; ethanol; hexane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(98)00508-0

upstream raw materials:

potassium cyanide

(2R,4R,1'R)-2-(1'-benzyloxy-4'-oxohexadecyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester

1-dodecylbromide

(2R,4R)-2-carboxy-4-phenyl-3-tert-butoxycarbonyloxazolidine

Downstream raw materials:

(3R,5S,8R,8aR)-8-Benzyloxy-5-dodecyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine

(2S,3R,6S)-3-benzyloxy-N-benzyloxycarbonyl-6-dodecyl-2-vinylpiperidine

(2S,3R,6S)-3-benzyloxy-N-benzyloxycarbonyl-6-dodecyl-2-hydroxymethylpiperidine

(2S,3R,6S,1'R)-2-(3-benzyloxy-6-dodecyl-2-vinylpiperidine-1-yl)-2-phenylethanol