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Chemical Structure| 710973-92-5 Chemical Structure| 710973-92-5

Structure of 710973-92-5

Chemical Structure| 710973-92-5

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Product Details of [ 710973-92-5 ]

CAS No. :710973-92-5
Formula : C14H26N2O2
M.W : 254.37
SMILES Code : O=C(N1CCC(NCC2CC2)CC1)OC(C)(C)C
MDL No. :MFCD12106421

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Application In Synthesis of [ 710973-92-5 ]

* 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 [ 710973-92-5 ]

[ 710973-92-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 710973-92-5 ]
  • [ 90176-80-0 ]
  • 4-[cyclopropylmethyl-(4-fluoro-2-trifluoromethyl-benzyl)-amino]-piperidine-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
82.2% In a 3-L double JACKETED-REACTOR with overhead stirring (anchor-type), secondary amine (104g) is dissolved in THF (ROLAND-L. OL; 0.05% w/v water). Powdered NaHB (OAc) 3 (104. 0g ; 1.2 equiv) and 2-trifluoromethyl-4-fluoro-benzaldehyde (66.7 mL; 1.1 equiv) are added. Mass temperature rises from rt= 22. 5C to 27. 3C within 40min and then slowly decreases to rt= 22. 5C.). After 8h, powdered NaHB (OAc) 3 (21. 5g ; 0.25 equiv) and 2-trifluoromethyl-4-fluoro- benzaldehyde (11.1 mL; 0.2 equiv) are added. Mixture is allowed to stir overnight at rt= 22. 5C. After 23H, 1H NMR ratio of starting material vs product is 1: 5.4. NaHB (OAc) 3 (21. 5g ; 0.25 equiv) and 2-trifluoromethyl-4-fluoro-benzaldehyde (11.1 mL; 0.2 equiv) are added. One hour later, ratio is 1: 5.8. Reaction is allowed to stir at RT=23C for another 24H. LH NMR ratio of starting material vs product after a total OF 48H is 1: 20. Reaction is left under minimum stirring for the weekend. The mixture is cooled down to 0C and water (400 mL) is added (ATM=12. 5C). Once ATm max is reached, Tj is set to 20C. Once TM=20C, MTBE (800mL) is added. Layers are separated and aqueous layer, whose pH=5-6, is extracted by MTBE (400mL). Organic layers are pooled and washed with NAOH 2N (2x400mL), NaCl 10% (2x 400 mL) and evaporated to dryness to yield tertiary amine containing 2-trifluoromethyl-4-fluororbenzylic alcohol (221.7g- 82.2% area).
  • 2
  • [ 710973-92-5 ]
  • [ 75-16-1 ]
  • [ 90176-80-0 ]
  • {cyclopropylmethyl-[1-(4-fluoro-2-trifluoromethyl-phenyl)-ethyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% Benzotriazole (326 mg, 2.75 mmol) and 4- (CYCLOPROPYHNETHYL-AMINO)-PIPERIDINE-L- carboxylic acid TERT-BUTYL ester (700 mg, 2.75 mmol) were dissolved in dry benzene (30 mL). 4-fluoro-2-trifluoromethyl benzaldehyde (0.38 mL, 2.75 mmol) was then added and the reaction was heated under reflux for overnight with a Dean-Stark trap. The reaction mixture was concentrated and the crude was dissolved in dry THF (20 mL). The reaction was cooled to 0C and methylmagnesium bromide (3.0 M solution in ET20, 1.1 mL, 3.02 mmol) was added dropwise. The reaction was stirred at ambient temperature for 1 hour. The reaction was quenched with saturated ammonium chloride and extracted with ethyl acetate (2X). The combined organic extracts were washed with aqueous saturated sodium chloride, dried (NA2S04), filtered and concentrated. The crude product was purified by flash chromatography on silica gel eluting with 25% EtOAc/hexane to yield (174mg, 14%) of {CYCLOPROPYIMETHYL- [L- (4-FLUORO-2-TRIFLUOROMETHYL-PHENYL)- ethyl]-amino}-piperidine-l-carboxylic acid TERT-BUTYL ester: mass spectrum (ion spray): M/Z == 445.1 (M+1) ;'H NMR (400 MHz, CD30D) : 8 = 8.13-8. 05 (1H, m), 7.43-7. 36 (2H, m), 4.43-4. 34 (1H, m), 4.17-4. 03 (2H, m), 2.76-2. 46 (4H, m), 2.27 (1H, dd, J=14. 9,7. 0 Hz), 1.81-1. 71 (1H, m), 1.68-1. 34 (16H, m), 0.88-0. 77 (1H, m), 0.51-0. 44 (2H, M), 0. 13-- 0.04 (2H, M).
 

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