(3R,5S,8aR)-5-((R)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile

Base Information

• Chemical Name: (3R,5S,8aR)-5-((R)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile
• CAS No.: 1025961-96-9
• Molecular Formula: C₂₂H₂₂N₂O₄
• Molecular Weight: 378.428
• Mol file: 1025961-96-9.mol

Synonyms:(3R,5S,8aR)-5-((R)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile

Chemical Property of (3R,5S,8aR)-5-((R)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-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,8aR)-5-((R)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile

There total 1 articles about (3R,5S,8aR)-5-((R)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-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:

piperonal (120-57-0,30024-74-9) + (-)-2-cyano-6-phenyloxazolopiperidine (88056-92-2) → (3R,5S,8aR)-5-((R)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile (1025961-96-9)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction; 1.) hexane, THF, -78 deg C, 45 min, 2.) THF, -78 deg C, 10 min;

DOI:10.1016/S0040-4020(01)89913-0

Reference yield: 99.0%

(3R,5S,8aR)-5-((R)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile (1025961-96-9) → (R)-2-[(R)-2-((R)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-piperidin-1-yl]-2-phenyl-ethanol (152088-23-8)

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 12h; Heating;

DOI:10.1016/S0040-4020(01)89913-0

Reference yield:

(3R,5S,8aR)-5-((R)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile (1025961-96-9) → (1R,3R,8aR)-1-Benzo[1,3]dioxol-5-yl-3-(3,4,5-trimethoxy-phenyl)-hexahydro-oxazolo[3,4-a]pyridine

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / NaBH₄ / ethanol / 12 h / Heating

2: 99 percent / H₂ / 10percent Pd/C / ethanol / 12 h / 760 Torr

3: 80 percent / p-TsOH / toluene / 12 h / Heating

With sodium tetrahydroborate; hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In ethanol; toluene;

DOI:10.1016/S0040-4020(01)89913-0

upstream raw materials:

piperonal

(-)-2-cyano-6-phenyloxazolopiperidine

Downstream raw materials:

(R)-2-[(R)-2-((R)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-piperidin-1-yl]-2-phenyl-ethanol

[(R)-2-((R)-Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-piperidin-1-yl]-(3,4,5-trimethoxy-phenyl)-methanone

(1R,3R,8aR)-1-(6-Bromo-benzo[1,3]dioxol-5-yl)-3-(3,4,5-trimethoxy-phenyl)-hexahydro-oxazolo[3,4-a]pyridine

[(R)-2-((R)-Benzo[1,3]dioxol-5-yl-benzyloxy-methyl)-piperidin-1-yl]-(3,4,5-trimethoxy-phenyl)-methanone