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Chemical Structure| 146873-76-9 Chemical Structure| 146873-76-9

Structure of 146873-76-9

Chemical Structure| 146873-76-9

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Product Details of [ 146873-76-9 ]

CAS No. :146873-76-9
Formula : C14H25NO3
M.W : 255.35
SMILES Code : O=C(N1CCC(CCCC=O)CC1)OC(C)(C)C

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Application In Synthesis of [ 146873-76-9 ]

* 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 [ 146873-76-9 ]

[ 146873-76-9 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 142355-83-7 ]
  • [ 146873-76-9 ]
YieldReaction ConditionsOperation in experiment
Step C 4-(1-t-Butoxycarbonylpiperidin-4-yl)butanal The title compound was prepared from 200 mg (0.79 mmol) of 4-(1-t-butoxycarbonylpiperidin-4-yl)butan-1-ol (from EXAMPLE 103, Step B) using a procedure analogous to that described in EXAMPLE 1, Step I. 153 mg (77%) of the title compound was obtained: 1H NMR (500 MHz) δ 1.10 (dq, J=4.4, 8.2, 2H). 1.25-1.30 (2H), 1.38-1.44 (m, 1H), 1.46 (s, 9H), 1.63-1.69 (4H), 2.44 (dt, J=1.7, 5.7, 2H). 2.67 (bt, 2H), 4.8 (bs, 2H), 9.77 (t, J=1.8, 1H).
With Dess-Martin periodane; In dichloromethane; at 0 - 20℃; for 1h; Preparation 11: 4-(4-Oxobutyl)piperidine-l-carboxylic acid tert-butyl esterA stirred suspension of Dess-Martin periodinane (165 mg, 391 μmol) in CH2Cl2 (3 mL) was cooled on ice and a solution of 4-(4-hydroxybutyl)piperidine-l-carboxylic acid tert-butyl ester in CH2Cl2 (2 mL) added. Stirring was continued for 1 h at rt whereupon the solvent was evaporated and the residue taken up in ether (20 mL). The organic phase was washed with brine (3 mL), dried (MgSO4) and evaporated. The residue was purified by column chromatography (IH-Et2O 2:1) to afford the title aldehyde: δH (CDCl3) 1.09 (dq, 2H), 1.25-1.30 (m, 2H), 1.36- 1.45 (m, IH), 1.46 (s, 9H), 1.62-1.70 (m, 4H), 2.44 (t, 2H), 2.68 (t, 2H), 4.08 (m, 2H), 9.78 (s, IH).
With pyridinium chlorochromate; In dichloromethane; at 0 - 20℃; for 3h; To a mixture of tert-butyl 4-( 4-hydroxybutyl)piperidine-1-carboxylate (2 g, 7.8 mmol) inDCM (40 mL) cooled to 0 oc was added pyridinium chlorochromate (2.5 g, 11.7 mmol). The mixture was stirred at room temperature for 3 h. Then the mixture was poured into ether(500 mL) and filtered. The filtrate was washed with water until the aqueous phase was colorless.The organic phase was dried and concentated to give tert-butyl 4-( 4-oxobutyl )piperidine-1-carboxylate. LRMS m/z (M+Na) 278.1 found, 278.2 required.
1.427 g To a solution of oxalyl chloride (757.49 mg, 5.968 mmol, 1.2 equiv) in DCM (7.5 ml_) was added DMSO (408.01 mg, 5.222 mmol, 1 .05 equiv) in DCM (8.00 ml_) dropwise at -78 C under nitrogen atmosphere. The resulting mixture was stirred for 5 min at -78 C followed by addition of tert-butyl 4-(4- hydroxybutyl)piperidine-1-carboxylate (1.28 g, 4.973 mmol, 1.00 equiv) in DCM (6.5 ml_). The resulting mixture was stirred for additional 15 min at -78 C, followed by the addition of TEA (2.52 g, 24.867 mmol, 5 equiv) at -78 C. The resulting mixture was stirred for additional 10 min at -78 C, warmed to room temperature, and stirred for an additional 2 hours. The mixture was extracted with CH2CI2 (3 x 20 ml_). The combined organic layers were washed with brine (3 x 30 ml_), dried over anhydrous Na2SC>4. After filtration, the filtrate was concentrated under reduced pressure. This provided Intermediate 2 (1 .427 g) as a light yellow oil; LCMS (ESI) m/z: [M+H]+ = 256.

 

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