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Structure of 142929-48-4

Chemical Structure| 142929-48-4

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Product Details of [ 142929-48-4 ]

CAS No. :142929-48-4
Formula : C9H15NO4
M.W : 201.22
SMILES Code : O=C(N1C(COCC1)=O)OC(C)(C)C
MDL No. :MFCD09751120
InChI Key :HJYNLENYMULSAS-UHFFFAOYSA-N
Pubchem ID :15000282

Safety of [ 142929-48-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 142929-48-4 ]

* 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 [ 142929-48-4 ]

[ 142929-48-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 109-11-5 ]
  • [ 24424-99-5 ]
  • [ 142929-48-4 ]
YieldReaction ConditionsOperation in experiment
94.21% With dmap; triethylamine; In dichloromethane; at 20℃; for 16h; To a solution of <strong>[109-11-5]morpholin-3-one</strong> (6.4 g, 63.30 mmol, 1.0 eq) in DCM (100 mL) at 20 C was added TEA (19.22 g, 189.90 mmol, 26.4 mL, 3.0 eq), DMAP (1.55 g, 12.66 mmol, 0.2 eq) and then Boc2O (27.63 g, 126.60 mmol, 29.1 mL, 2.0 eq), and the resulting mixture was stirred at 20 C for 16 h. The reaction mixture was concentrated to remove the solvent and the residue was diluted with water (200 mL) and extracted with EA (100 mL *3). The combined organic layers were washed with water (50 mL *3) and then brine (100 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by flash silica gel chromatography to give tert-butyl 3-oxomorpholine-4- carboxylate (12.0 g, 59.64 mmol, 94.21% yield) as yellow oil. 1H NMR (400 MHz, CDCI3) δ 4.23 (s, 2H), 3.93 - 3.87 (m, 2H), 3.79 - 3.72 (m, 2H), 1.55 (s, 9H). di-tert-butyl 3-oxomorpholine-2,4-dicarboxylate
76% With dmap; In tetrahydrofuran; at 20℃; for 24h; Step 1: 7¾ri-butyl 3-oxomorpholine- -carboxylate [00197] Morpholin-3-one (35g, 346.2 mmol) was slurried in dry THF (350ml). Tert- butoxycarbonyl tert- butyl carbonate (105.8g, 11 1.4 mmol) was added, followed by DMAP (4.2g, 34.6 mmol). The mixture began to degass rapidly over 30 minutes. The resulting orange solution was stirred at ambient temperature for 24hrs. The mixture was then cooled in an ice bath and imidazole (23.57g, 346.2 mmol) was added. After stirring for 30 minutes ethyl acetate (500ml) was added. The organic phase was separated and washed with 1% (v/v) HC1 (500ml), then sat NaHC03 (500ml), then brine (200ml), dried (MgS04), filtered and concentrated. The crude was purified through a plug of silica gel, eluting with ethyl acetate. The filtrate was evaporated to give an oil. 40/60 pet ether (200ml) was added slowly with stirring to generate a white solid. The mixture was aged for 30 minutes, cooled briefly in an ice bath and filtered, washing with 40/60 pet ether. Tert-butyl 3-oxomorpholine-4- carboxylate was obtained as a white solid which was dried under vacuum (52.7g, 76%); lH- NMR (CDCI3) 1.47 (9H, s), 3.68 (2H, m), 3.82 (2H, m), 4.15 (2H, s); MS ES(+) 145.8 (M+ - tBu).
66% With dmap; In tetrahydrofuran; at 20℃;Inert atmosphere; Morpholmn-3-one (8.00 g, 79.2 mmcl) was dissolved in dry THE (100 mL), and then (Boc)20 (25.9 g, 0.119 mol) and DMAP (966 mg, 7.92 mmol) were added. The mixture was stirred at room temperature under N2 atmosphere overnight. Imidazole (5.39 g, 79.2 mmol) was added. After stirred for 30 mm EtOAc (150 mL) was added. The organic layer was washed with brine (100 mL), dried over Na2SO4, filtered and concentrated in vacuo to give oil whichwas solidified after standing. The solid was washed with PE (100 mL)to afford the desired compound (10.5 g, yield 66%) as a white solid.1H NMR (300 MHz, CDCI3): 64.20 (s, 2H), 3.88-3.85 (m, 2H), 3.74-3.70 (m, 2H), 1.51 (s, 9H).LC-MS (mobile phase: from 95% water and 5% CH3CN to 5% water and 95% CH3CN in 3.0mm, purity is >95%, Rt = 1.56 mm; MS Calcd.: 201; MS Found: 202 [M+H] 146 [M-56+H].
 

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