(4S,5R)-4-benzyloxy-1-(4-methoxybenzyl)-5-cyclohexylmethyl-2-pyrrolidinone

Base Information

• Chemical Name: (4S,5R)-4-benzyloxy-1-(4-methoxybenzyl)-5-cyclohexylmethyl-2-pyrrolidinone
• CAS No.: 335162-36-2
• Molecular Formula: C₂₆H₃₃NO₃
• Molecular Weight: 407.553
• Mol file: 335162-36-2.mol

Synonyms:(4S,5R)-4-benzyloxy-1-(4-methoxybenzyl)-5-cyclohexylmethyl-2-pyrrolidinone

Chemical Property of (4S,5R)-4-benzyloxy-1-(4-methoxybenzyl)-5-cyclohexylmethyl-2-pyrrolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-4-benzyloxy-1-(4-methoxybenzyl)-5-cyclohexylmethyl-2-pyrrolidinone

There total 1 articles about (4S,5R)-4-benzyloxy-1-(4-methoxybenzyl)-5-cyclohexylmethyl-2-pyrrolidinone 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:

cyclohexylmethyl magnesium bromide (35166-78-0) + (S)-4-benzyloxy-1-(4-methoxybenzyl)-2,5-pyrrolidinedione (254730-07-9) → (4S,5R)-4-benzyloxy-1-(4-methoxybenzyl)-5-cyclohexylmethyl-2-pyrrolidinone (335162-36-2)

Guidance literature:

cyclohexylmethyl magnesium bromide; (S)-4-benzyloxy-1-(4-methoxybenzyl)-2,5-pyrrolidinedione; In tetrahydrofuran; at -10 - 10 ℃;

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃; for 17h;

DOI:10.1016/S0957-4166(03)00442-7

Reference yield: 67.0%

(4S,5R)-4-benzyloxy-1-(4-methoxybenzyl)-5-cyclohexylmethyl-2-pyrrolidinone (335162-36-2) → (4S,5R)-4-benzyloxy-5-cyclohexylmethyl-2-pyrrolidinone (335162-37-3)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at 0 - 23 ℃;

DOI:10.1016/S0957-4166(03)00442-7

Reference yield:

(4S,5R)-4-benzyloxy-1-(4-methoxybenzyl)-5-cyclohexylmethyl-2-pyrrolidinone (335162-36-2) → (3S,4R)-4-[(tert-butyloxycarbonyl)amino]-5-cyclohexyl-3-hydroxypentanoic acid ethyl ester (607685-52-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 67 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0 - 23 °C

2: 92 percent / DMAP; Et₃N / tetrahydrofuran / 14 h / 20 °C

3: 91 percent / formic acid / Pd/C / methanol / 2 h / 20 °C

4: 95 percent / KCN / tetrahydrofuran / 36 h / 20 °C

With dmap; potassium cyanide; formic acid; ammonium cerium(IV) nitrate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; water; acetonitrile;

DOI:10.1016/S0957-4166(03)00442-7

upstream raw materials:

cyclohexylmethyl magnesium bromide

(S)-4-benzyloxy-1-(4-methoxybenzyl)-2,5-pyrrolidinedione

Downstream raw materials:

(4S,5R)-4-benzyloxy-5-cyclohexylmethyl-2-pyrrolidinone

(3S,4R)-4-[(tert-butyloxycarbonyl)amino]-5-cyclohexyl-3-hydroxypentanoic acid ethyl ester

(4S,5R)-1-(tert-butyloxycarbonyl)-4-hydroxy-5-cyclohexylmethyl-2-pyrrolidinone

(4S,5R)-4-benzyloxy-1-(tert-butyloxycarbonyl)-5-cyclohexylmethyl-2-pyrrolidinone