(R)-6-[(S)-1-(benzyloxy)propyl]-1,2,3,6-tetrahydropyridine

Base Information

• Chemical Name: (R)-6-[(S)-1-(benzyloxy)propyl]-1,2,3,6-tetrahydropyridine
• CAS No.: 1403599-36-9
• Molecular Formula: C₁₅H₂₁NO
• Molecular Weight: 231.338
• Mol file: 1403599-36-9.mol

Synonyms:(R)-6-[(S)-1-(benzyloxy)propyl]-1,2,3,6-tetrahydropyridine

Chemical Property of (R)-6-[(S)-1-(benzyloxy)propyl]-1,2,3,6-tetrahydropyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-6-[(S)-1-(benzyloxy)propyl]-1,2,3,6-tetrahydropyridine

There total 5 articles about (R)-6-[(S)-1-(benzyloxy)propyl]-1,2,3,6-tetrahydropyridine 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: 72.0%

(3R,4S)-4-(benzyloxy)-N-(but-3-enyl)-1-phenylhex-1-en-3-amine (1403599-35-8) → (R)-6-[(S)-1-(benzyloxy)propyl]-1,2,3,6-tetrahydropyridine (1403599-36-9)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; toluene-4-sulfonic acid; In dichloromethane; for 6h; Inert atmosphere; Reflux;

DOI:10.1002/ejoc.201200489

Reference yield:

C27H28ClNO5S → (R)-6-[(S)-1-(benzyloxy)propyl]-1,2,3,6-tetrahydropyridine (1403599-36-9)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium sulfite / water; toluene / 6 h / 20 °C / Inert atmosphere

2: water; potassium hydroxide / dimethyl sulfoxide / 48 h / 0 - 80 °C / Inert atmosphere

3: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 - 60 °C / Inert atmosphere

4: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; toluene-4-sulfonic acid / dichloromethane / 6 h / Inert atmosphere; Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; water; potassium carbonate; toluene-4-sulfonic acid; potassium hydroxide; sodium sulfite; In dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1002/ejoc.201200489

Reference yield:

(3R,4S,Z)-4-(benzyloxy)-1-phenylhex-1-en-3-amine (1403599-34-7) → (R)-6-[(S)-1-(benzyloxy)propyl]-1,2,3,6-tetrahydropyridine (1403599-36-9)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 - 60 °C / Inert atmosphere

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; toluene-4-sulfonic acid / dichloromethane / 6 h / Inert atmosphere; Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; potassium carbonate; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201200489

upstream raw materials:

(3R,4S,Z)-4-(benzyloxy)-1-phenylhex-1-en-3-amine

(3R,4S)-4-(benzyloxy)-N-(but-3-enyl)-1-phenylhex-1-en-3-amine

benzyl (3R,4S)-4-(benzyloxy)-1-phenylhex-1-en-3-ylcarbamate

Downstream raw materials:

(S)-1-[(R)-piperidin-2-yl]propan-1-ol [(-)-α-conhydrine]

Refernces