2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric acid Chemical Properties

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

InChI

InChI=1/C10H19NO4.C4H6O6/c1-10(2)14-8-6(11)5-7(9(8)15-10)13-4-3-12;5-1(3(7)8)2(6)4(9)10/h6-9,12H,3-5,11H2,1-2H3;1-2,5-6H,(H,7,8)(H,9,10)/t6-,7+,8+,9-;1-,2-/s3

InChIKey

XEYNXCGNMKWIDO-PLHQUINWNA-N

SMILES

[C@H](O)(C(=O)O)[C@@H](O)C(=O)O.O([C@H]1C[C@@H](N)[C@]2([H])OC(C)(C)O[C@]12[H])CCO |&1:0,5,11,13,15,22,r|

Safety Information

Safety Statements 

24/25

HS Code 

29329990

2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric acid Usage And Synthesis

Chemical Properties

White to off-white powder

Uses

2-[[(3aR,4S,6R,6aS)-6-aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-Ethanol (2R,3R)-2,3-dihydroxybutanedioate is a useful building block, most frequently used in the preparation of the antithrombotic agent Ticagrelor.

Synthesis

Put 50g of benzyl ((3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)carbamate and 250 mL of methanol into a 1L four-necked flask 1.Add 10 g of 10% palladium carbon and 22.4 g of ammonium formate to bottle 1 at 20-30°C. After the addition, the temperature is raised to 40-50°C, and the reaction is stirred for 10 hours and filtered with suction. The filtrate was transferred to a 1L four-neck flask 2, and the temperature was raised to 40-50°C again. 21.4g L-tartaric acid was added to batches 2 while stirring. Then, continue to stir the reaction for 1 hour, slowly lower the temperature to 10-20°C, and stir the reaction for 2 hours, and a large number of white solids can be seen to precipitate. Continue to lower the temperature to 0-10°C and react for 0.5h, then suction filter and wash the filter cake once with 50mL ethanol. The filter cake was dried under reduced pressure at 40° C. for 4 hours to obtain 45.7 g of white powdery solid 2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric acid with a yield of 87.47%.

Application

2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric acid could be used to synthesis 2-[((3aR,4S,6R,6aS)-6-{[5-nitro-6-chloro-2-(propylthio)- 4-pyrimidinyl]amino}-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxoI-4-yl)oxy]-1-ethanol.

2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric acid(376608-65-0)Related Product Information

• tert-butyl 1-(2,5-difluorophenyl)-1-oxopent-4-yn-2-ylcarbaMate
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• TICAGRELOR
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• (3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol
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• 1-Acetyladamantane Intermediate
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• Ethanol, 2-[[(3aR,4S,6R,6aS)-6-[[5-aMino-6-chloro-2-(propylthio)-4-pyriMidinyl]aMino]tetrahydro-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-
• ethyCyclopropanamine, 2-(3,4-difluorophenyl)-, (1R,2S)- (REACH)
• (1R,2R)-2-(3,4-difluorophenyl)cyclopropane carboxaMide
• (1R trans)-2-(3,4-difluorophenyl)cyclopropane amine
• CarbaMicacid,N-[(3aS,4R,6S,6aR)-tetrahydro-6-hydroxy-2,2-diMethyl-4H-cyclopenta-1,3-dioxol-4-yl]-,phenylMethyl ester
• Cyclopropanamine,2-(3,4-difluorophenyl)-(1R,2S) -(2R,3R)-2,3-dihydroxybutanedioate (1:1)