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Chemical Structure| 540501-56-2 Chemical Structure| 540501-56-2

Structure of 540501-56-2

Chemical Structure| 540501-56-2

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Product Details of [ 540501-56-2 ]

CAS No. :540501-56-2
Formula : C11H21NO3
M.W : 215.29
SMILES Code : O=C(N1[C@H](CO)C[C@H](C)C1)OC(C)(C)C
MDL No. :MFCD22421683

Safety of [ 540501-56-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Application In Synthesis of [ 540501-56-2 ]

* 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 [ 540501-56-2 ]

[ 540501-56-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 540501-56-2 ]
  • [ 364750-81-2 ]
YieldReaction ConditionsOperation in experiment
94% With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; sodium dihydrogenphosphate; In water; acetonitrile; at 40 - 45℃; for 19h;pH 6.6; Following the method of Del Valle and Goodman, three solutions were prepared prior to the oxidation. The first solution consisted of NaClO2 (1.33 g, 14.7 mmol) in water (7.4 mL). The second solution consisted of bleach (436 muL) in water (7.4 mL). The third solution consisted of compound 8 (1.60 g, 7.4 mmol) dissolved in 100 mL of 3:2 CH3CN:NaH2PO4 buffer (pH 6.6, 0.67 M). The solution containing 8 was heated to 45° C., and TEMPO (193 mg, 0.7 mmol) was added. The two oxidant solutions were added simultaneously in 618 muL portions over 1 h, and the resulting solution was stirred at 40° C. for 18 h. After cooling to room temperature, the reaction was quenched by dropwise addition of saturated aqueous Na2SO3 until the solution became colorless. The acetonitrile was removed under reduced pressure, and the resulting aqueous solution basified to pH 10 with 1 M NaOH. The basic solution was washed with ether (5*125 mL) and then acidified to pH 2 with 2 M HCl. The acidic solution was extracted with ether (4*200 mL), and the organic layer was dried over anhydrous MgSO4(s) and concentrated under reduced pressure to afford 9 (1.60 g, 7.0 mmol, 94percent) as a white solid. 1H NMR delta: 1.09 (d, J=6.0, 3H), 1.44 and 1.50 (s, 9H), 1.58-1.70 and 1.88-2.00 (m, 1H), 2.21-2.31 (m, 1H), 2.31-2.52 (m, 1H), 2.89-3.04 (m, 1H), 3.67-3.82 (m, 1H), 4.20-4.38 (2m, 1H); 13C NMR delta: 16.9, 17.2, 28.2, 28.3, 32.7, 36.4, 38.8, 53.3, 54.1, 59.4, 59.5, 80.4, 81.6, 159.4, 162.1, 174.9, 179.6; ESI-MS (m/z): [M-H]- calcd for C11H18NO4, 228.1; found, 228.4.
  • 2
  • [ 364750-81-2 ]
  • [ 540501-56-2 ]
YieldReaction ConditionsOperation in experiment
100% With diborane; In tetrahydrofuran; at 0 - 20℃; for 2h; To a solution of compound 20- 1 (1 .12 g. 4.88 mmol) in THF (10.0 mL) at 0 °C was added borane (7.3 mL, 1 M in THF). and the mixture was stirred at rt for 2 hrs. After the reaction was completed, the mixture was quenched with MeOH (4.0 mL). The solvent THF was removed in vacuo, and the residue was dissolved in DCM (50 mL). The solution was washed with water (20 mL x 3), dried over anhydrous Na2S04 and concentrated in vacuo, and the residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 3/1 ) to give the title compound as colorless slurry (1.03 g. 100percent). The compound was characterized by the following spectroscopic data: MS (ESI. pos.ion) mlz: 216.29 [M+H] +; NMR (400 MHz. CDC13) delta (ppm): 4.02 (s, 1 H). 3.99-3.87 (m, 1 H), 3.75-3.68 (m. 1 H), 3.66 (dd, 1 H, J = 11.6 Hz, 2.0 Hz), 3.57 (dd, 1H, J = 1 1.6 Hz. 7.4 Hz), 2.76 (t, 1H, J = 10.5 Hz), 2.19-2.06 (m, 2H), 1.46 (s, 9H). 1.01 (d, 3H, J = 6.2 Hz).
100% With borane-THF; In tetrahydrofuran; at 0 - 20℃; To a solution of compound 10-1 (1.12 g, 4.88 mmol) in THF (10 mL) at 0 °C was added borane (7.3 mL, 1 M in THF) dropwise slowly. At the end of the addition, the mixture was stirred at rt for 2 hours. After the reaction was completed, the mixture was quenched with methanol (4 mL) and concentrated in vacuo. The residue was dissolved in DCM (50 mL). The solution was washed with water (20 mL x 3) and a saturated aqueous solution of NaCl, dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 3/1) to give the title compound as colorless oil (1.05 g, 100percent). The compound was characterized by the following spectroscopic data: MS (ESI, pos.ion) mlz: 216.3 [M+H]+; and NMR (400 MHz, CDC13): delta 4.02 (s, 1H), 3.99-3.87 (m, 1H), 3.75-3.68 (m, 1H), 3.66 (dd, 1H, J = 11.6 Hz, 2.0 Hz), 3.57 (dd, 1H, J= 11.6 Hz, 7.4 Hz), 2.76 (t, 1H, J= 10.5 Hz), 2.19-2.06 (m, 2H), 1.46 (s, 9H), 1.01 (d, 3H, J= 6.2 Hz) ppm.
100% With diborane; In tetrahydrofuran; at 20℃; for 2h; 11283] To a solution of compound 20-1 (1.12 g, 4.88 mmol) in THF (10.0 mE) at 0° C. was added borane (7.3 mE, 1 M in THF), and the mixture was stirred at it for 2 hrs. Afier the reaction was completed, the mixture was quenched with MeOH (4.0 mE). The solvent THF was removed in vacuo, and the residue was dissolved in DCM (50 mE). The solution was washed with water (20 mEx3), dried over anhydrous Na2504 and concentrated in vacuo, and the residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=3/1) to give the title compound as colorless slurry (1.03 g, 100percent). The compound was characterized by the following spectroscopic data:11284] MS (ESI, pos.ion) mlz: 216.29 [M+H]11285] ?H NMR (400 MHz, CDC13) oe (ppm): 4.02 (s, 1H),3.99-3.87 (m, 1H), 3.75-3.68 (m, 1H), 3.66 (dd, 1H, J=11.6 Hz, 2.0 Hz), 3.57 (dd, 1H, J=11.6 Hz, 7.4 Hz), 2.76 (t, 1H, J=10.5 Hz), 2.19-2.06 (m, 2H), 1.46 (s, 9H), 1.01 (d, 3H, J=6.2 Hz).
100% With borane-THF; In tetrahydrofuran; at 0 - 20℃; for 2h;Inert atmosphere; Compound 8-1 (1.12 g, 4.88 mmol) was dissolved in THF (10 mL) and borane (7.3mL, 1M in THF) was slowly added dropwise at 0 ° C. After the addition was completed,the mixture was stirred at rt for 2.0 hours. After the reaction was completed, thereaction was quenched with methanol (4.0 mL), the THF was removed and the residue was dissolved in DCM (50 mL), washed with water (20 mL x 3) and saturated brine,respectively, 2SO 4Dried and concentrated. The residue was purified by columnchromatography (eluent: PE / EtOAc (v / v) = 3/1) to give 1.05 g of a colorless syrup.Yield: 100percent.

 

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