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[ CAS No. 477293-60-0 ] {[proInfo.proName]}

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Chemical Structure| 477293-60-0
Chemical Structure| 477293-60-0
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Product Details of [ 477293-60-0 ]

CAS No. :477293-60-0 MDL No. :MFCD20278358
Formula : C10H19NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :BXZADLGAYWRZCR-YUMQZZPRSA-N
M.W : 201.26 Pubchem ID :56846373
Synonyms :

Safety of [ 477293-60-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 477293-60-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 477293-60-0 ]

[ 477293-60-0 ] Synthesis Path-Downstream   1~12

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  • C32H43NO3S [ No CAS ]
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YieldReaction ConditionsOperation in experiment
100% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 20.5h;Inert atmosphere; Mesyl chloride (0.125 mL, 1.61 mmol) was added to a stirred solution of (2LU)-4- hydroxy-2-methyl-pyrrolidine-l -carboxylic acid tert- butyl ester (CAS: 477293-60-0; 250 mg, 1.24) in DCM (5 mL) at 0 C under nitrogen atmosphere. Then, DIPEA (0.368 mL, 2.11 mmol) was added at 5 C over 5 min. The mixture was stirred at 5 C for 30 min, then was stirred at rt for 20 h. The mixture was diluted with an NaHC03 aq. sat. sol and extracted with DCM. The organic layer was separated, dried (MgS04), filtered and the solvents evaporated in vacuo to yield intermediate (350 mg, 100%) as a brown sticky solid.
87% With triethylamine; In dichloromethane; at 0 - 18℃; for 2.0h; To a solution of tert-butyl (2S,4S)-4-hydroxy-2-methylpyrrolidine-l-carboxylate (200 mg, 0.994 mmol) and TEA (201 mg, 1.99 mmol) in DCM (10 mL) was added methanesulfonyl chloride (228 mg, 1.99 mmol) at 0C. After addition, the mixture was stirred at 18C for 2 h. The reaction was quenched with aq. NaHCCL (8 mL) and extracted with DCM (10 mL x 3). The combined organics were dried (I^SCL) and evaporatedScheme to dryness to give the title compound as a yellow oil (243 mg, 87%) which was used without further purification. LCMS: ([M-Boc+H] = 163.0).
67% With triethylamine; In dichloromethane; at 0℃; for 1.5h;Inert atmosphere; The reaction was performed in anhydrous conditions under Argon atmosphere. To a solution of <strong>[477293-60-0]tert-butyl (2S,4S)-4-hydroxy-2-methylpyrrolidine-1-carboxylate</strong> (2 g, 9.94 mmol) in DCM (32 mL) cooled at 0 C were added Et3N (2.67 mL, 19.2 mmol) and methanesulfonyl chloride (1.11 mL, 14.4 mmol) and the reaction mixture was stirred at 0 C for 1.5 h. Water (55 mL) was added and the aqueous layer was extracted with DCM (2 x 75 mL). The combined organic layers were washed with HC1 (IN, aq., 50 mL), NaHCCb (sat., aq., 50 mL), dried (NaiSCL), filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, mobile phase: cyclohexane/EtOAc, gradient from 80/20 to 40/60) to afford tert-butyl (2S,4S)-2-methyl-4-((methylsulfonyl)oxy)pyrrolidine-1-carboxylate 131 (1.97 g, 67%) as a colorless oil.
With triethylamine; In dichloromethane; at 0℃; for 16.0h; Intermediate 81,1 -dimethylethyl (2S,4S)-2-methyl-4-[(methylsulfonyl)oxy]-1-pyrrolidinecarboxylate1 ,1-dimethylethyl (2S,4S)-4-hydroxy-2-methyl-1-pyrrolidinecarboxylate (1.0326 g,5.13 mmol) in DCM (~2 mL) was placed under argon and cooled to 0 0C. To the reaction mixture was added triethylamine (1.2973 g, 12.8 mmol) and methanesulfonyl chloride (1.1753 g, 10.3 mmol). The resultant mixture was stirred for 16 hours and diluted in ether (-100 mL) and water (-60 mL). The aqueous layer was extracted with ethyl acetate (x2). The organic layers were combined, washed with 1 N HCI and NaHCO3 solution, dried on MgSO4 and the solvent evaporated under vacuum to afford the title compound as a yellow liquid (0.6395 g). LC-MS: m/z, 280 (M+H).

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YieldReaction ConditionsOperation in experiment
99.5% With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 10.0h;Cooling with ice; Step 2 [0412] Compound iv-8 (2.52g, 7.99mmol) was dissolved in THF (13mL). To the solution was added 1mol/L tetra butylammonium fluoride in THF (15.97mL, 15.97mmol) under ice-cooling, and the mixture was stirred for 10 hours under ice-cooling. To the reaction mixture was added water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed by water and brine, and concentrated in vacuo to give Compound IV-4 (1.6g, Yield 99.5%). [0413] 1H-NMR (CDCl3) δ: 4.42-4.39 (1H, m), 4.02-3.99 (1H, m), 3.49-3.46 (2H, m), 2.11-2.08 (1H, m), 1.76-1.73 (1H, br m), 1.57-1.53 (1H, m), 1.47 (9H, s), 1.24 (3H, t, J = 5.26 Hz).
With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20℃; for 3.0h; Intermediate 7 1,1 -dimethylethyl-(2S,4S)-4-hydroxy-2-methyl-1 -pyrrolidinecarboxylateTo 1 ,1-dimethylethyl (2S,4S)-4-[(1 ,1-dimethylethyl)(dimethyl)silyl]oxy}-2-methyl-1- pyrrolidinecarboxylate (0.19201 g, 6.08 mmol) in THF (~1 ml.) was added TBAF (12 ml_,12.17 mmol) under argon. The resultant mixture was stirred at room temperature for 3 hours and purified by flash chromatography (silica gel) with gradient ethyl acetate:hexanes(1 :2) to (2:1 ) to afford the title compound (1.0326 g). LC-MS: m/z, 202 (M+H).
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