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Chemical Structure| 554451-12-6 Chemical Structure| 554451-12-6

Structure of 554451-12-6

Chemical Structure| 554451-12-6

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Product Details of [ 554451-12-6 ]

CAS No. :554451-12-6
Formula : C12H21NO4
M.W : 243.30
SMILES Code : O=C([C@@H]1C[C@H](NC(OC(C)(C)C)=O)CC1)OC
MDL No. :MFCD19381777

Safety of [ 554451-12-6 ]

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 [ 554451-12-6 ]

* 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 [ 554451-12-6 ]

[ 554451-12-6 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 261165-05-3 ]
  • [ 554451-12-6 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; methanol; hexane; Example 195A <strong>[261165-05-3](1S,3R)-3-tert-butoxycarbonylamino-cyclopentanecarboxylic acid</strong> methyl ester To a cold solution (0 C.) of Example 191A (458 mg, 2 mmol)in THF (2 mL)/MeOH (2 mL) was added TMSCHN2 (2 mL, 2N in hexane). The mixture was stirred at room temperature for 2 hours, concentrated under reduced pressure and purified by flash chromatography with 30% acetone/hexane to provide the titled compound. MS (ESI) m/z 244 (M+H)+.
  • 2
  • [ 554451-12-6 ]
  • [ 261165-05-3 ]
YieldReaction ConditionsOperation in experiment
To a solution of methyl czs-3-[(fer^butoxycarbonyl)amino]cyclopentanecarboxylate (70.9 g) in MeOH (300 mL) was added aqueous NaOH (NaOH 12.2 g, H2O 15.0 mL). The mixture was stirred at ambient temperature for 16 h and the mixture was evaporated under reduced pressure. To the residue was added 5% KHSO4 (250 mL). The precipitate was collected by filtration and dried at 800C under reduced pressure to give a white solid (87.7 g). To the suspension of above solid (66.8 g) in toluene (500 mL) were added diphenylphosphoryl azide (84.2 g) in toluene (50.0 mL) and Et3N (35.4 g) in toluene (50.0 mL) and the mixture was stirred at 100 0C for 35 min. To the mixture was added benzyl alcohol (33.1 g). The mixture was stirred at 130 0C for 2 h and evaporated under reduced pressure. To the residue were added EtOAc (800 mL) and H2O (600 mL) and the organic layer was EPO <DP n="104"/>separated. The organic layer was dried over MgSO4, filtered, concentrated under reduced pressure and purified by flush chromatography (silica gel, 13% to 25% EtOAc in hexane) to give the title compound (43.8 g).1HNMR (200 MHz, CDCl3, delta): 1.26-1.71 (m, 12H), 1.81-2.08 (m, 2H), 2.30-2.52 (m, IH), 3.82-4.09 (m, 2H), 4.69-4.88 (m, IH), 5.00-5.20 (m, 3H), 7.26-7.41 (m, 5H); ESI MS m/z 335 (M++l, 20%).
  • 3
  • [ 74-88-4 ]
  • [ 261165-05-3 ]
  • [ 554451-12-6 ]
YieldReaction ConditionsOperation in experiment
Preparation 86 2-((1S,3R)-3-Aminocyclophentyl)propan-2-ol Step (a): (+)-(1 S,3R)-N-Boc-3-Aminocyclopentane carboxylic acid (355mg, 1.55mmol) and cesium carbonate (252mg, 0.774mmol) were dissolved in methanol (3ml) and the resulting solution was evaporated in vacuo. The residue was suspended in dry toluene and concentrated in vacuo twice. The residue was then dissolved in dry DMF (5ml), iodomethane (290 ml_,4.64mmol) was added and the resulting solution was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and partitioned between DCM and water and the organic phase was dried, concentrated and purified by silica column chromatography eluting with a gradient of DCM to 5% MeOH:DCM to give 224mg of (1S 3R)-3-tert- butoxycarbonlyamino-cyclopentanecarboxylic acid methyl ester as a pale yellow oil.1H NMR (CDCI3, 400 MHz): delta ppm 1.44(s, 9H), 1.62(m, 1 H), 1.70(m, 1 H), 1.92(m, 3H), 2.21 (m, 1 H), 2.83(m, 1 H), 3.69(s, 3H), 4.04(broad 1 H),4.91 (broad, 1 H).
 

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