tert-butyl (2SR,3RS)-2-amino-3-cyclohexyl-3-hydroxypropanoate

Base Information

• Chemical Name: tert-butyl (2SR,3RS)-2-amino-3-cyclohexyl-3-hydroxypropanoate
• CAS No.: 228858-52-4
• Molecular Formula: C₁₃H₂₅NO₃
• Molecular Weight: 243.346
• Mol file: 228858-52-4.mol

Synonyms:tert-butyl (2SR,3RS)-2-amino-3-cyclohexyl-3-hydroxypropanoate

Chemical Property of tert-butyl (2SR,3RS)-2-amino-3-cyclohexyl-3-hydroxypropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2SR,3RS)-2-amino-3-cyclohexyl-3-hydroxypropanoate

There total 3 articles about tert-butyl (2SR,3RS)-2-amino-3-cyclohexyl-3-hydroxypropanoate 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:

N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) + cyclohexanecarbaldehyde (2043-61-0) → tert-butyl (2SR,3RS)-2-amino-3-cyclohexyl-3-hydroxypropanoate (228858-52-4) + tert-butyl (2SR,3SR)-2-amino-3-cyclohexyl-3-hydroxypropanoate

Guidance literature:

N-(diphenylmethylene)glycine tert-butyl ester; cyclohexanecarbaldehyde; With sodium hydroxide; (R,R)-2,2'-binaphtyl derivative quaternary ammonium salt; at 0 ℃; for 3h;

With hydrogenchloride; In tetrahydrofuran; for 1h;

DOI:10.1021/ja048865q

Reference yield:

N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) → tert-butyl (2SR,3RS)-2-amino-3-cyclohexyl-3-hydroxypropanoate (228858-52-4)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium diisopropylamide / tetrahydrofuran / -78 °C

2: 1.) cinchonidine-derived bifluoride salt; 2.) aq. citric acid / 1.) hexane, CH₂Cl₂, -50 deg C, 1 h; 2.) THF, r.t.

With cinchonidine-derived bifluoride salt; citric acid; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(99)00636-X

Reference yield:

benzhydrylidene-(2-tert-butoxy-2-trimethylsilanyloxy-vinyl)-amine + cyclohexanecarbaldehyde (2043-61-0) → (2S,3S)-2-Amino-3-cyclohexyl-3-hydroxy-propionic acid tert-butyl ester + tert-butyl (2SR,3RS)-2-amino-3-cyclohexyl-3-hydroxypropanoate (228858-52-4)

Guidance literature:

With cinchonidine-derived bifluoride salt; citric acid; Yield given; Multistep reaction. Yields of byproduct given; 1.) hexane, CH₂Cl₂, -50 deg C, 1 h; 2.) THF, r.t.;

DOI:10.1016/S0040-4039(99)00636-X

upstream raw materials:

cyclohexanecarbaldehyde

N-(diphenylmethylene)glycine tert-butyl ester