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[ CAS No. 117565-57-8 ]

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2D
Chemical Structure| 117565-57-8
Chemical Structure| 117565-57-8
Structure of 117565-57-8 *Storage: {[proInfo.prStorage]}

Quality Control of [ 117565-57-8 ]

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Related Doc. of [ 117565-57-8 ]

SDS

Product Details of [ 117565-57-8 ]

CAS No. :117565-57-8MDL No. :MFCD08460961
Formula :C12H21NO3Boiling Point :-
Linear Structure Formula :-InChI Key :-
M.W :227.30Pubchem ID :22278903
Synonyms :

Computed Properties of [ 117565-57-8 ]

TPSA : 46.6 H-Bond Acceptor Count : 3
XLogP3 : 1.5 H-Bond Donor Count : 0
SP3 : 0.83 Rotatable Bond Count : 3

Safety of [ 117565-57-8 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 117565-57-8 ]

  • Upstream synthesis route of [ 117565-57-8 ]
  • Downstream synthetic route of [ 117565-57-8 ]

[ 117565-57-8 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 104777-74-4 ]
  • [ 24424-99-5 ]
  • [ 117565-57-8 ]
YieldReaction ConditionsOperation in experiment
83%
Stage #1: With triethylamine In methanol; dichloromethane at 23℃; for 16.00 h;
Stage #2: With sodium hydroxide In water
Compound 26 (2.90 g, 10.2 mmol) was suspended in 6 N HCl (85 ml) and refluxed for 16 h. The product was concentrated and azeotroped three times with isopropanol to give a yellow solid. The solid was dissolved in 1:1 CH2Cl2:MeOH (50 ml) and Et3N (3.08 g, 4.3 ml, 30.5 mmol) and di-t-butyl dicarbonate (3.32 g, 15.2 mmol) were added. The mixture was stirred at 23° C. for 16 h, then concentrated. 0.5 N NaOH (50 ml) was added and the mixture extracted with CH2Cl2. The combined organic extracts were dried (MgSO4), filtered, and concentrated. Purification by silica gel chromatography (eluant: 10percent EtOAc-hexane) gave 1.92 g (8.46 mmol, 83percent) of the product 27A as a colorless oil. MS (ES for M+1): m/e 228
Reference: [1] Patent: US2005/182095, 2005, A1. Location in patent: Page/Page column 30
  • 2
  • [ 79099-07-3 ]
  • [ 75-03-6 ]
  • [ 117565-57-8 ]
YieldReaction ConditionsOperation in experiment
680 mg With toluene-4-sulfonic acid In benzene for 16.00 h; Reflux Step 1
A solution of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (5 g, 25.1 mmol), pyrolidine (5 mL) and p-toluenesulfonic acid (25 mg) in benzene (100 mL) was heated at reflux for 16 h with azeotropic distillation of water.
The resulting enamine solution was cooled to rt and concentrated.
The crude enamine was dissolved in acetonitrile (50 mL); iodoethane (4.67 g, 30.1 mmoL) was added and the mixture was heated at 100° C. for 0.5 h, cooled to rt and concentrated.
The mixture was dissolved in ethyl acetate (200 mL), washed with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate, and brine.
The extract was dried over magnesium sulfate, filtered and concentrated.
The crude compound was purified by silica gel chromatography (80percent hexanes/20percent ethyl acetate) to afford 3-ethyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (680 mg).
1H-NMR (CDCl3, 300 MHz) δ: 0.95 (t, 3H), 1.26-1.42 (m, 1H), 1.50 (s, 9H), 1.69-1.85 (m, 1H), 2.30 (br s, 1H), 2.43 (q, 2H), 2.90-4.36 (m, 4H).
Reference: [1] Patent: US2005/70549, 2005, A1
[2] Patent: US2016/31908, 2016, A1. Location in patent: Paragraph 1320; 1321
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