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

Base Information

• Chemical Name: (4S,5R)-1-(tert-butyloxycarbonyl)-4-hydroxy-5-cyclohexylmethyl-2-pyrrolidinone
• CAS No.: 607685-51-8
• Molecular Formula: C₁₆H₂₇NO₄
• Molecular Weight: 297.395
• Mol file: 607685-51-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (4S,5R)-1-(tert-butyloxycarbonyl)-4-hydroxy-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: 91.0%

(4S,5R)-4-benzyloxy-1-(tert-butyloxycarbonyl)-5-cyclohexylmethyl-2-pyrrolidinone (335162-38-4) → (4S,5R)-1-(tert-butyloxycarbonyl)-4-hydroxy-5-cyclohexylmethyl-2-pyrrolidinone (607685-51-8)

Guidance literature:

With formic acid; palladium on activated charcoal; In methanol; at 20 ℃; for 2h;

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

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (4S,5R)-1-(tert-butyloxycarbonyl)-4-hydroxy-5-cyclohexylmethyl-2-pyrrolidinone (607685-51-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / DMAP; Et₃N / tetrahydrofuran / 14 h / 20 °C

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

With dmap; formic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol;

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

Reference yield:

cyclohexylmethyl magnesium bromide (35166-78-0) → (4S,5R)-1-(tert-butyloxycarbonyl)-4-hydroxy-5-cyclohexylmethyl-2-pyrrolidinone (607685-51-8)

Guidance literature:

Multi-step reaction with 4 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

4.1: 91 percent / formic acid / Pd/C / methanol / 2 h / 20 °C

With dmap; formic acid; ammonium cerium(IV) nitrate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; water; acetonitrile; 1.1: Grignard reaction;

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

upstream raw materials:

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

di-tert-butyl dicarbonate

cyclohexylmethyl magnesium bromide

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

Downstream raw materials:

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