scholarly journals An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its Optimization

2019 ◽  
Vol 2019 ◽  
pp. 1-8
Author(s):  
Qi Liao ◽  
Lan Jiang ◽  
Cong Li ◽  
Yaling Shen ◽  
Min Wang ◽  
...  
Keyword(s):  
Sulfuric Acid ◽  
Nitric Acid ◽  
Potassium Permanganate ◽  
Practical Method ◽  
Commercial Production ◽  
Target Compound ◽  
One Pot ◽  
Adamantanecarboxylic Acid ◽  
The One

A mild and relatively simple way for preparation of 2-(3-hydroxy-1-adamantane)-2-oxoacetic acid (I) was reported. It was prepared from 1-adamantanecarboxylic acid (II) via sulfuric acid/nitric acid to get 3-hydroxy-1-adamantanecarboxylic acid (III); treated with the one-pot method through acylation, condensation, and decarboxylation to obtain 3-hydroxy-1-acetyladamantane (IV); and finally oxidized by potassium permanganate (KMnO4) to get the target compound (I). The overall yield was about 60%, which provides a new idea for commercial production of saxagliptin intermediate.

Nano-sphere silica sulfuric acid: novel and efficient catalyst in the one-pot multi-component synthesis

2013 ◽  
Vol 10 (6) ◽  
pp. 1297-1301 ◽  
Author(s):  
Ardeshir Khazaei ◽  
Mohammad Ali Zolfigol ◽  
Mohammad Mokhlesi ◽  
Rahele Rostamian
Keyword(s):  
Sulfuric Acid ◽  
Silica Sulfuric Acid ◽  
One Pot ◽  
Efficient Catalyst ◽  
The One

Silica Sulfuric Acid: An Efficient and Reusable Catalyst for the One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones.

ChemInform ◽  
2003 ◽  
Vol 34 (27) ◽  
Author(s):  
Peyman Salehi ◽  
Minoo Dabiri ◽  
Mohammad Ali Zolfigol ◽  
Mohammad Ali Bodaghi Fard
Keyword(s):  
Sulfuric Acid ◽  
Reusable Catalyst ◽  
Silica Sulfuric Acid ◽  
One Pot ◽  
One Pot Synthesis ◽  
The One

Silica sulfuric acid magnetic nanoparticle: an efficient and ecofriendly catalyst for synthesis of spiro[2-amino-4H-pyran-oxindole]s

2015 ◽  
Vol 93 (5) ◽  
pp. 546-549 ◽  
Author(s):  
Ali Reza Karimi ◽  
Meysam Sourinia ◽  
Zeinab Dalirnasab ◽  
Marzie Karimi
Keyword(s):  
Sulfuric Acid ◽  
Magnetic Nanoparticle ◽  
Ultrasound Irradiation ◽  
Significant Loss ◽  
Silica Sulfuric Acid ◽  
One Pot ◽  
External Magnet ◽  
Three Component Reaction ◽  
The One ◽  
High Yields

Silica sulfuric acid magnetic nanoparticles efficiently catalyze the one-pot, three-component reaction of isatins and malononitrile with dimedone, 1,3-dimethylbarbituric acid or 4-hydroxycoumarin in EtOH–H2O to afford the corresponding spiro[2-amino-4H-pyran-oxindole] derivatives in high yields under ultrasound irradiation at 60 °C. The heterogeneous nanocatalyst could be recovered easily from the reaction mixture using an external magnet and reused many times without significant loss of its catalytic activity.

Xanthan Sulfuric Acid as an Efficient Biodegradable and Recyclable Catalyst for the One-Pot Synthesis of α-Amino Phosphonates

2010 ◽  
Vol 57 (6) ◽  
pp. 1315-1320 ◽  
Author(s):  
Guo-Ying Sun ◽  
Jun-Tao Hou ◽  
Jing-Jie Dou ◽  
Jun Lu ◽  
Yong-Jie Hou ◽  
...  
Keyword(s):  
Sulfuric Acid ◽  
Recyclable Catalyst ◽  
One Pot ◽  
One Pot Synthesis ◽  
The One ◽  
Amino Phosphonates

Annulations leading to diene systems. Total syntheses of the dolastane-type diterpenoids (±)-(5S,12R,14S)-dolasta-1(15),7,9-trien-14-ol and (±)-amijitrienol

1992 ◽  
Vol 70 (4) ◽  
pp. 1204-1220 ◽  
Author(s):  
Edward Piers ◽  
Richard W. Friesen
Keyword(s):  
Aldol Condensation ◽  
Ring Closure ◽  
Starting Material ◽  
Target Compound ◽  
One Pot ◽  
Stereoselective Reduction ◽  
Total Syntheses ◽  
Reductive Transformation ◽  
The One ◽  
Key Steps

Alkylation of the substituted cycloalkanones 14a–d and 30 with (Z)-1-bromo-4-methyl-3-trimethylstannyl-2-pentene (13) produced compounds 15a–d and 33, which were readily converted into the corresponding enol trifluoromethane-sulfonates (triflates) 16a–d and 34. Intramolecular Pd(O)-catalyzed coupling of the vinylstannane and enol triflate functions in 16a–d and 34 provided the dienes 17a–d and 35. The annulation product 35 served as a suitable starting material for the total syntheses of the dolastane diterpenoids (±)-(5S,12R,14S)-dolasta-1(15),7,9-trien-14-ol (2) and (±)-amijitrienol (3). The key steps of the synthesis of (±)-2 involved the stereoselective methylation of the ketone 44 (readily derived from 35) to provide 46 and the Barbier type ring closure of 47 to provide the target compound. For the synthesis of (±)-3, the notable conversions included the reductive transformation of the diene 35 into the alkene 53, the aldol condensation of the ketone 54 with 4-trimethylstannyl-4-pentenal (55), the chemo- and stereoselective reduction of the dione 58, and the one-pot conversion of the keto vinylstannane 63 into the triene 65, via the intermediate 64.

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