(2S,4R)-1-Boc-2-cyano-4-hydroxypyrrolidine

Base Information

• Chemical Name: (2S,4R)-1-Boc-2-cyano-4-hydroxypyrrolidine
• CAS No.: 483366-12-7
• Molecular Formula: C10H16N2O3
• Molecular Weight: 212.249
• Hs Code.: 2933998090
• Mol file: 483366-12-7.mol

Synonyms:1-Pyrroli;tert-Buty;LogP

Chemical Property of (2S,4R)-1-Boc-2-cyano-4-hydroxypyrrolidine

Chemical Property:

• Vapor Pressure: 1.11E-06mmHg at 25°C
• Refractive Index: 1.511
• Boiling Point: 361.4 °C at 760 mmHg
• PKA: 13.90±0.40(Predicted)
• Flash Point: 172.4 °C
• PSA: 73.56000
• Density: 1.19 g/cm³
• LogP: 0.81818
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

(2S,4R)-1-Boc-2-cyano-4-hydroxypyrrolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-1-Boc-2-cyano-4-hydroxypyrrolidine

There total 4 articles about (2S,4R)-1-Boc-2-cyano-4-hydroxypyrrolidine 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: 74.0%

tert-butyl (2S,4R)-2-(aminocarbonyl)-4-hydroxypyrrolidine-1-carboxylate (109384-24-9) → (2S,4R)-N-Boc-2-cyano-4-hydroxypyrrolidine (483366-12-7)

Guidance literature:

With trifluoroacetic anhydride; In pyridine; at -20 - 20 ℃; for 24h;

Reference yield: 50.0%

tert-butyl (2S,4R)-2-cyano-4-benzoyloxypyrrolidine-1-carboxylate (1000616-48-7) → (2S,4R)-N-Boc-2-cyano-4-hydroxypyrrolidine (483366-12-7)

Guidance literature:

With ammonia; In methanol; at 5 - 10 ℃; for 2 - 3h;

Reference yield:

4-(methylsulfonyl)benzonitrile (22821-76-7) + (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → (2S,4R)-N-Boc-2-cyano-4-hydroxypyrrolidine (483366-12-7) + N-Boc-2-cyano-4-hydroxypyrrolidine

Guidance literature:

With riboflavin-2',3',4',5'-tetra-acetate; In acetonitrile; at 25 ℃; for 7h; Overall yield = 60 %; Overall yield = 31.8 mg; Inert atmosphere; Irradiation; Sealed tube;

DOI:10.1021/acs.orglett.9b00064

upstream raw materials:

tert-butyl (2S,4R)-2-cyano-4-benzoyloxypyrrolidine-1-carboxylate

tert-butyl (2S,4R)-2-(aminocarbonyl)-4-hydroxypyrrolidine-1-carboxylate

(4R)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile

Refernces

• 1、 Le Vaillant, Franck,Wodrich, Matthew D.,Waser, Jér?me. "Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation". . p. 1790 - 1800. Retrieved 2017/03/09.
• 2、 -. "NOVEL PROCESSES FOR THE PREPARATION OF DPP IV INHIBITORS". Page/Page column 43. . Retrieved 2008/06/13.