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

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

10synthesis methods

Product Name:2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric acid
CAS Number:376608-65-0
Molecular formula:C14H25NO10
Molecular Weight:367.35

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%.

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

N-[(3aS,4R,6S,6aR)-Tetrahydro-6-(2-hydroxyethoxy)-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamic acid phenylmethyl ester

274693-54-8
73 suppliers
$20.00/100mg

87-69-4 Synthesis

87-69-4
873 suppliers
$5.00/25g

376608-65-0
353 suppliers
$9.00/1g

Yield:376608-65-0 87.47%

Reaction Conditions:

Stage #1: benzyl 6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ylcarbamatewith palladium 10% on activated carbon;ammonium formate in methanol at 20 - 50; for 10 h;
Stage #2: L-Tartaric acid at 10 - 50; for 3 h;

Steps:

4-5 Example 5: Preparation of Compound IV

Put 50g of compound III (the preparation method adopts any one of the methods of Example 1 to Example 3) 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, and 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, and 21.4g L-tartaric acid was added in batches to 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 amount 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 compound IV with a yield of 87.47% and a GC purity of 99.56% (after free extraction of compound IV with alkali).

References:

CN112724119,2021,A Location in patent:Paragraph 0044-0049

274693-53-7 Synthesis