1-(1,1-Dimethylethyl) (2S,4S)-4-(methoxymethyl)-1,2-pyrrolidinedicarboxylate
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1-(1,1-Dimethylethyl) (2S,4S)-4-(methoxymethyl)-1,2-pyrrolidinedicarboxylate
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CAS No:
1378388-16-9
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Formula:
C12H21NO5
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Chemical Name:
1-(1,1-Dimethylethyl) (2S,4S)-4-(methoxymethyl)-1,2-pyrrolidinedicarboxylate
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Synonyms:
1,2-Pyrrolidinedicarboxylic acid,4-(methoxymethyl)-,1-(1,1-dimethylethyl) ester,(2S,4S)-;1-(1,1-Dimethylethyl) (2S,4S)-4-(methoxymethyl)-1,2-pyrrolidinedicarboxylate;(2S,4S)-1-(tert-Butoxycarbonyl)-4-(methoxymethyl)pyrrolidine-2-carboxylic acid;N-tert-Butoxycarbonyl-(4S)-4-Methoxymethyl-L-proline
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CAS No:
1-(1,1-Dimethylethyl) (2S,4S)-4-(methoxymethyl)-1,2-pyrrolidinedicarboxylate Basic Attributes
259.29884
259.30
807-416-9
1-(1,1-Dimethylethyl) (2S,4S)-4-(methoxymethyl)-1,2-pyrrolidinedicarboxylate Use and Manufacturing
In a clean 500 ml four-necked flask, (2S, 4S)-1-(tert-butoxycarbonyl)-4-(methoxymethyl)pyrrolidine-2-carboxylic acid dicyclohexylamine salt 16 g was added. 75 ml of water, 75 ml of methyl tert-butyl ether, adjusted to pH by adding sodium hydroxide solution, and phase separated. Methyl tert-butyl ether was added to the aqueous phase, the temperature was controlled to be less than 25 C, the pH was adjusted with a hydrochloric acid solution, the phases were separated, and the aqueous phase was extracted once more with methyl t-butyl ether. The combined organic phases were washed once with a saturated aqueous solution of sodium chloride. The organic layer was collected, and the organic layer was dried over anhydrous sodium sulfate. Filtration, the solvent was evaporated to dryness under reduced pressure, and hexane and dichloromethane were added, and the mixture was heated to 60 C to dissolve into a clear solution.It was cooled to a solid precipitate, cooled, filtered, washed with hexane and dried to give 9.0 g of white solid.Yield = 96%, de% = 96%.Compound 3 (10g, 31.7mmol, leq) was dissolved in 50ml THF was added NaOH (1 · 52g, 38 · Ommol, 1.2eq) aqueous solution (6 ml of), stirred at room temperature 6h, TLC the reaction was complete. The reaction solution was adjusted to pH 6 ~ 8 and extracted with dichloromethane (50ml X2), the organic layers were combined, dried over anhydrous sodium sulfate, and concentrated. The residue using hexane: dichloromethane recrystallized from about 7.3g white solid in a yield of 90.8%Add 6.7 g (25.8 mmol) of iii-7 to 100 ml of tetrahydrofuran and stir to dissolve.Drop on ice bath3.4 ml of a solution of 1.0 M (34 mmol) borane dimethyl sulfide solution. Stir at 0C for 4 hours, It is then stirred at room temperature for 18 hours. The mixture was then cooled to 0[deg.] C. and 70 ml of methanol was added dropwise. Stir and raise to room temperature. It is evaporated to dryness under reduced pressure and 200 ml of dichloromethane is added.Wash with saturated sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate overnight and evaporated to dryness under reduced pressure.(2S, 4S)-N-(tert-butyloxycarbonyl)-2-hydroxymethyl-4-(methoxymethyl)-pyrrolidine (iii-8) 6.1 g was obtained.Step 7: Add 6.7 g (25.8 mmol) of iii-7 to 100 ml of tetrahydrofuran, stir to dissolve, and add 3.4 ml of 1.0M (34 mmol) dropwise on an ice bath.Borane dimethyl sulfide solution. Stir at 0C for 4 hours, It is then stirred at room temperature for 18 hours. The mixture was then cooled to 0C and 70 ml of methanol was added dropwise. Stirring, Gradually rise to room temperature. Distilled under reduced pressure, add 200ml dichloromethaneWash with saturated sodium bicarbonate.The organic layer was dried over anhydrous sodium sulfate overnight and evaporated to dryness under reduced pressure.(2S, 4S)-N-(tert-butyloxycarbonyl)-2-hydroxymethyl-4-(methoxymethyl)-pyrrolidine (iii-8) 6.1 g
Computed Properties
Molecular Weight:259.30
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:5
Exact Mass:259.14197277
Monoisotopic Mass:259.14197277
Topological Polar Surface Area:76.1
Heavy Atom Count:18
Complexity:323
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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1-(1,1-Dimethylethyl) (2S,4S)-4-(methoxymethyl)-1,2-pyrrolidinedicarboxylate
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