(2R,3S)-3-(4-cyanophenoxy)-2-(hydroxymethyl)-1-<(1,1-dimethylethoxy)carbonyl>pyrrolidine

Base Information

• Chemical Name: (2R,3S)-3-(4-cyanophenoxy)-2-(hydroxymethyl)-1-<(1,1-dimethylethoxy)carbonyl>pyrrolidine
• CAS No.: 144610-80-0
• Molecular Formula: C₁₇H₂₂N₂O₄
• Molecular Weight: 318.373
• Mol file: 144610-80-0.mol

Synonyms:(2R,3S)-3-(4-cyanophenoxy)-2-(hydroxymethyl)-1-<(1,1-dimethylethoxy)carbonyl>pyrrolidine

Chemical Property of (2R,3S)-3-(4-cyanophenoxy)-2-(hydroxymethyl)-1-<(1,1-dimethylethoxy)carbonyl>pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-(4-cyanophenoxy)-2-(hydroxymethyl)-1-<(1,1-dimethylethoxy)carbonyl>pyrrolidine

There total 6 articles about (2R,3S)-3-(4-cyanophenoxy)-2-(hydroxymethyl)-1-<(1,1-dimethylethoxy)carbonyl>pyrrolidine 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: 97.0%

(2R,3S)-3-(4-cyanophenoxy)-2-<<((1,1-dimethylethyl)dimethylsilyl)oxy>methyl>-1-<(1,1-dimethylethoxy)carbonyl>pyrrolidine (144610-79-7) → (2R,3S)-3-(4-cyanophenoxy)-2-(hydroxymethyl)-1-<(1,1-dimethylethoxy)carbonyl>pyrrolidine (144610-80-0)

Guidance literature:

In tetrahydrofuran; water; acetic acid; at 45 ℃;

DOI:10.1016/S0040-4039(01)93413-6

Reference yield:

4-cyanophenol (767-00-0) → (2R,3S)-3-(4-cyanophenoxy)-2-(hydroxymethyl)-1-<(1,1-dimethylethoxy)carbonyl>pyrrolidine (144610-80-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / PPh₃, diethyl azodicarboxylate (DEAD) / tetrahydrofuran / 18 h / 25 °C

2: 91 percent / aq. AcOH / tetrahydrofuran / 18 h / 45 °C

With acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1021/ja00052a015

Reference yield:

(2R,3S)-1-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyloxy)methyl]-3-hydroxypyrrolidine (216229-02-6) → (2R,3S)-3-(4-cyanophenoxy)-2-(hydroxymethyl)-1-<(1,1-dimethylethoxy)carbonyl>pyrrolidine (144610-80-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / PPh₃, diethyl azodicarboxylate (DEAD) / tetrahydrofuran / 18 h / 25 °C

2: 91 percent / aq. AcOH / tetrahydrofuran / 18 h / 45 °C

With acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1021/ja00052a015

upstream raw materials:

(2R,3S)-3-(4-cyanophenoxy)-2-<<((1,1-dimethylethyl)dimethylsilyl)oxy>methyl>-1-<(1,1-dimethylethoxy)carbonyl>pyrrolidine

4-cyanophenol

(2R,3S)-1-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyloxy)methyl]-3-hydroxypyrrolidine

tert-butyl (2R,3R)-2-[(tert-butyldimethylsiloxy)methyl]-3-hydroxypyrrolidine-1-carboxylate

Downstream raw materials:

(2S,3S)-3-(4-cyanophenoxy)-1-<(1,1-dimethylethoxy)carbonyl>proline

methyl (2S,3S)-3-(4-formylphenoxy)-1-<(1,1-dimethylethoxy)carbonyl>prolinate

methyl (2S,3S)-3-(4-cyanophenoxy)-1-<(1,1-dimethylethoxy)carbonyl>prolinate

methyl (2S,3S)-3-<4-(2-nitro-1-hydroxyethyl)phenoxy>-1-<(1,1-dimethylethoxy)carbonyl>prolinate