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

Base Information

• Chemical Name: (4S,5R)-4-benzyloxy-1-(tert-butyloxycarbonyl)-5-cyclohexylmethyl-2-pyrrolidinone
• CAS No.: 335162-38-4
• Molecular Formula: C₂₃H₃₃NO₄
• Molecular Weight: 387.519
• Mol file: 335162-38-4.mol

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

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

There total 4 articles about (4S,5R)-4-benzyloxy-1-(tert-butyloxycarbonyl)-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: 92.0%

di-tert-butyl dicarbonate (24424-99-5) + (4S,5R)-4-benzyloxy-5-cyclohexylmethyl-2-pyrrolidinone (335162-37-3) → (4S,5R)-4-benzyloxy-1-(tert-butyloxycarbonyl)-5-cyclohexylmethyl-2-pyrrolidinone (335162-38-4)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; at 20 ℃; for 14h;

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

Reference yield:

cyclohexylmethyl magnesium bromide (35166-78-0) → (4S,5R)-4-benzyloxy-1-(tert-butyloxycarbonyl)-5-cyclohexylmethyl-2-pyrrolidinone (335162-38-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran / -10 - 10 °C

1.2: 1.437 g / Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 17 h / -78 - 20 °C

2.1: 67 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0 - 23 °C

3.1: 92 percent / DMAP; Et₃N / tetrahydrofuran / 14 h / 20 °C

With dmap; ammonium cerium(IV) nitrate; triethylamine; In tetrahydrofuran; water; acetonitrile; 1.1: Grignard reaction;

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

Reference yield:

(S)-4-benzyloxy-1-(4-methoxybenzyl)-2,5-pyrrolidinedione (254730-07-9) → (4S,5R)-4-benzyloxy-1-(tert-butyloxycarbonyl)-5-cyclohexylmethyl-2-pyrrolidinone (335162-38-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran / -10 - 10 °C

1.2: 1.437 g / Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 17 h / -78 - 20 °C

2.1: 67 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0 - 23 °C

3.1: 92 percent / DMAP; Et₃N / tetrahydrofuran / 14 h / 20 °C

With dmap; ammonium cerium(IV) nitrate; triethylamine; In tetrahydrofuran; water; acetonitrile; 1.1: Grignard reaction;

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

upstream raw materials:

di-tert-butyl dicarbonate

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

cyclohexylmethyl magnesium bromide

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

Downstream raw materials:

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

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