(5S,6R)-5-Benzyloxy-6-(4-hydroxy-butyl)-1-(4-methoxy-benzyl)-piperidin-2-one

Base Information

• Chemical Name: (5S,6R)-5-Benzyloxy-6-(4-hydroxy-butyl)-1-(4-methoxy-benzyl)-piperidin-2-one
• CAS No.: 885111-44-4
• Molecular Formula: C₂₄H₃₁NO₄
• Molecular Weight: 397.514
• Mol file: 885111-44-4.mol

Synonyms:(5S,6R)-5-Benzyloxy-6-(4-hydroxy-butyl)-1-(4-methoxy-benzyl)-piperidin-2-one

Chemical Property of (5S,6R)-5-Benzyloxy-6-(4-hydroxy-butyl)-1-(4-methoxy-benzyl)-piperidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6R)-5-Benzyloxy-6-(4-hydroxy-butyl)-1-(4-methoxy-benzyl)-piperidin-2-one

There total 1 articles about (5S,6R)-5-Benzyloxy-6-(4-hydroxy-butyl)-1-(4-methoxy-benzyl)-piperidin-2-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:

(S)-3-benzyloxy-1-(4-methoxybenzyl)-2,6-piperidinedione (763105-88-0) + (4-((tert-butyldimethylsilyl)oxy)butyl)magnesium bromide → (5S,6R)-5-Benzyloxy-6-(4-hydroxy-butyl)-1-(4-methoxy-benzyl)-piperidin-2-one (885111-44-4) + (5S,6S)-5-Benzyloxy-6-(4-hydroxy-butyl)-1-(4-methoxy-benzyl)-piperidin-2-one

Guidance literature:

(S)-3-benzyloxy-1-(4-methoxybenzyl)-2,6-piperidinedione; (4-((tert-butyldimethylsilyl)oxy)butyl)magnesium bromide; In tetrahydrofuran; at -78 ℃; for 3h;

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/ol0602203

Reference yield: 92.0%

(5S,6R)-5-Benzyloxy-6-(4-hydroxy-butyl)-1-(4-methoxy-benzyl)-piperidin-2-one (885111-44-4) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid 4-[(2R,3S)-3-benzyloxy-1-(4-methoxy-benzyl)-6-oxo-piperidin-2-yl]-butyl ester (885111-45-5)

Guidance literature:

With pyridine; In dichloromethane; at -30 - -10 ℃;

DOI:10.1021/ol0602203

Reference yield:

(5S,6R)-5-Benzyloxy-6-(4-hydroxy-butyl)-1-(4-methoxy-benzyl)-piperidin-2-one (885111-44-4) → (1S,9aR)-1-Benzyloxy-octahydro-quinolizin-4-one (885111-47-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / pyridine / CH₂Cl₂ / -30 - -10 °C

2: 70 percent / CAN / acetonitrile; H₂O / 0 - 20 °C

3: 100 percent / NaH / tetrahydrofuran / -40 - 40 °C

With pyridine; ammonium cerium(IV) nitrate; sodium hydride; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1021/ol0602203

upstream raw materials:

(S)-3-benzyloxy-1-(4-methoxybenzyl)-2,6-piperidinedione

Downstream raw materials:

Toluene-4-sulfonic acid 4-[(2R,3S)-3-benzyloxy-1-(4-methoxy-benzyl)-6-oxo-piperidin-2-yl]-butyl ester

(1S,9aR)-1-Benzyloxy-octahydro-quinolizin-4-one

Toluene-4-sulfonic acid 4-((2R,3S)-3-benzyloxy-6-oxo-piperidin-2-yl)-butyl ester