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Chemical Structure| 845894-03-3 Chemical Structure| 845894-03-3

Structure of 845894-03-3

Chemical Structure| 845894-03-3

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Product Details of [ 845894-03-3 ]

CAS No. :845894-03-3
Formula : C9H14FNO3
M.W : 203.21
SMILES Code : CC(C)(C)OC(=O)N1CC(F)C(=O)C1
MDL No. :MFCD08274459
InChI Key :HPHVNLXMQXEDFX-UHFFFAOYSA-N
Pubchem ID :45158916

Safety of [ 845894-03-3 ]

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

Application In Synthesis of [ 845894-03-3 ]

* 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 [ 845894-03-3 ]

[ 845894-03-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 845894-03-3 ]
  • [ 95-00-1 ]
  • [ 885102-31-8 ]
YieldReaction ConditionsOperation in experiment
Add sodium triacetoxyborohydride (156 mg, 0.73 mmol) to a mixture of 3-fluoro- 4-oxopyrrolidine-l-carboxylic acid tert-butyl ester (100 mg, 0.5 mmol) and 2,4- dichlorobenzylamine (65 muL, 0.5 mmol) in 1,2-dichloroethane (1.5 mL), followed by 2 drops of glacial acetic acid and stir overnight at room temperature. Pour the crude mixture into 2 N sodium hydroxide and extract with ethyl acetate, wash with water, dry (magnesium sulfate), concentrate and chromatograph on silica gel to give 3 -(2,4- dichlorobenzylamino)-4-fluoropyrrolidine-l-carboxylic acid tert-butyl ester (40 mg, 20%). 1H NMR (300 MHz, CDCl3) delta 7.36-7.44 (2H, m), 7.20-7.28 (IH, m), 5.03 (IH, d, J = 54.07 Hz)5 3.21-3.95 (6H, m), 2.99-3.15 (IH, m), 1.45 (9H5 s), MS (ES): m/z = 363 [M+].
  • 2
  • trans-3-fluoro-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • [ 845894-03-3 ]
YieldReaction ConditionsOperation in experiment
With Dess-Martin periodane; In dichloromethane; at 0 - 20℃; Cool down a suspension of Dess Martin periodinane (279 mg, 0.65 mmol) in dry dichloromethane (1 mL) under nitrogen with an ice bath and add a solution of trans-3- fluoro-4-hydroxypyrrolidine-l-carboxylic acid tert-butyl ester (90 mg, 0.44 mmol) in dry dichloromethane (1 mL). Stir under nitrogen and allow to warm up to room temperature overnight. Add saturated aqueous sodium hydrogen carbonate, then saturated aqueous sodium thiosulfate and extract with dichloromethane. Combine the organic layers, wash with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give 3-fluoro-4-oxopyrrolidine-l-carboxylic acid tert-butyl ester which may be used without further purification. Characteristic peaks in the NMR include the proton alpha to the fluorine atom (5.01, IH, ddd, J = 51.52, 7.54, 7.25 Hz).
  • 3
  • [ 101385-93-7 ]
  • [ 845894-03-3 ]
YieldReaction ConditionsOperation in experiment
Step 1: (+-)-N-BOC-trans-3-fluoro-4(methylamnino)pyrrolidine 2-3 A cooled solution (-78 C.) of N-BOC-3-pyrrolidinone (1.0 g, 5.41 mmol) in THF (50 mL) was treated with a solution of NaHMDS (7.03 mL of a 1M soln in THF). After stirring for 30 min, the solution was treated with chlorotriethylsilane (1.18 mL, 7.03 mmol). The reaction was stirred for 1 hr at -78 C., warmed to 0 C., diluted with 1:1 brine/water and hexanes. The mixture was extracted with EtOAc. The organic solution was dried over Na2SO4, filtered, and concentrated. The residue was not further purified. A solution of the 3-fluoro-N-BOC-pyrrolidinone (0.31 g, 1.53 mmol) in dichloroethane (10 mL) was treated with methylarnine (1.53 mL of a 2M soln in THF) and Na(OAc)3BH (0.49 g, 2.3 mmol). After stirring for 12 h at room temperature, the reaction was diluted with EtOAc and washed with satd NaHCO3. The organic solution was dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (SiO2; 80% CHCl3/10% MeOH/10% EtOAc) to provide racemic 2-3. Data for 2-3: 1H-NMR (500 MHz, CDCl3) delta 5.11 (br d, J=55 Hz, 1H), 3.85-3.62 (m, 2H), 3.51 (m, 1H), 3.20 (m, 1H), 3.03 (m, 1H), 2.50 (s, 3H), 1.46 (s, 9H) ppm.
  • 4
  • [ 845894-03-3 ]
  • [ 74-89-5 ]
  • (-)-N-tert-butoxycarbonyl-trans-3-fluoro-4-methylamino-pyrrolidine [ No CAS ]
  • (+)-N-tert-butoxycarbonyl-trans-3-fluoro-4-methylamino-pyrrolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; In tetrahydrofuran; 1,2-dichloro-ethane; at 20℃; for 12.0h; Step 1: (+-)-N-BOC-trans-3-fluoro-4(methylamnino)pyrrolidine 2-3 A cooled solution (-78 C.) of N-BOC-3-pyrrolidinone (1.0 g, 5.41 mmol) in THF (50 mL) was treated with a solution of NaHMDS (7.03 mL of a 1M soln in THF). After stirring for 30 min, the solution was treated with chlorotriethylsilane (1.18 mL, 7.03 mmol). The reaction was stirred for 1 hr at -78 C., warmed to 0 C., diluted with 1:1 brine/water and hexanes. The mixture was extracted with EtOAc. The organic solution was dried over Na2SO4, filtered, and concentrated. The residue was not further purified. A solution of the 3-fluoro-N-BOC-pyrrolidinone (0.31 g, 1.53 mmol) in dichloroethane (10 mL) was treated with methylarnine (1.53 mL of a 2M soln in THF) and Na(OAc)3BH (0.49 g, 2.3 mmol). After stirring for 12 h at room temperature, the reaction was diluted with EtOAc and washed with satd NaHCO3. The organic solution was dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (SiO2; 80% CHCl3/10% MeOH/10% EtOAc) to provide racemic 2-3. Data for 2-3: 1H-NMR (500 MHz, CDCl3) delta 5.11 (br d, J=55 Hz, 1H), 3.85-3.62 (m, 2H), 3.51 (m, 1H), 3.20 (m, 1H), 3.03 (m, 1H), 2.50 (s, 3H), 1.46 (s, 9H) ppm.
 

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