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[ CAS No. 604010-24-4 ]

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2D
Chemical Structure| 604010-24-4
Chemical Structure| 604010-24-4
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Quality Control of [ 604010-24-4 ]

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Product Details of [ 604010-24-4 ]

CAS No. :604010-24-4MDL No. :MFCD19230157
Formula :C12H21NO3Boiling Point :308.2±35.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :227.30Pubchem ID :59662193
Synonyms :

Computed Properties of [ 604010-24-4 ]

TPSA : 46.6 H-Bond Acceptor Count : 3
XLogP3 : 1.4 H-Bond Donor Count : 0
SP3 : 0.83 Rotatable Bond Count : 2

Safety of [ 604010-24-4 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 604010-24-4 ]

  • Upstream synthesis route of [ 604010-24-4 ]
  • Downstream synthetic route of [ 604010-24-4 ]

[ 604010-24-4 ] Synthesis Path-Upstream   1~3

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YieldReaction ConditionsOperation in experiment
60.9% With triethylamine In dichloromethane at 27℃; for 16.00 h; Cooling with ice [0359] Preparation of tert-butyl 2,6-dimethyl-4-oxopiperidine-l-carboxylate (9.37): To an ice-cold solution of 2,6-dimethylpiperidin-4-one 9.36 (3.6 g, 28.34 mmol) in DCM (50 mL) was added Et3N (9.8 mL, 70.8 mmol) and boc anhydride (12.1 mL, 56.6 mmol). The resulting reaction mixture was stirred at RT for 16 h. After completion of the reaction (TLC monitoring), the reaction mass was diluted with water and extracted with DCM (3 times). The combined organics was washed with brine, dried over anhydrous Na2S04, filtered and concentrated. The crude was purified over silica gel (100-200 M, 10-15percent) EtOAc-hexane) to get the desired product 9.37 (3.9 g, Yield: 60.9percent). [0360] 1H-NMR (400 MHz, CDC13): δ 2.85 (d, J=6.4 Hz, 1H), 2.81 (d, J=6.4 Hz, 1H), 2.38-2.39 (m, 2H), 2.34-2.36 (m, 2H), 1.48 (s, 9H) and 1.25-1.27 (m, 6H). MS: 228.08 (M+H)+.
27% With dmap; triethylamine In dichloromethane at 20℃; for 16.00 h; To a solution of 2,6-dimethylpiperidin-4-one (0.7 g, 5.51 mmol) in DCM (10 mL) were added triethyl amine (1.5 mL, 11.02 mmol), DMAP (0.07 g, 0.55 mmol) and (Boc)2O (1.9 mL, 8.26 mmol) followed by stirring at RT for 16 h. The mixture was diluted with DCM and washed with water. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by combi- flash to afford the title compound as off white solid (0.34 g, 27 percent).1H NMR (400 MHz, DMSO-d6): δ 4.23-4.20 (m, 2H), 2.95-2.89 (m, 2H), 2.28 (s, 1H), 2.24 (s, 1H), 1.43 (s, 9H), 1.16 (d, J=6.8 Hz, 6H); ES-MS: m/z 128.2 (M-Boc)- .
Reference: [1] Patent: WO2015/103060, 2015, A1. Location in patent: Paragraph 0359-0360
[2] Patent: WO2016/203112, 2016, A1. Location in patent: Page/Page column 62; 63
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  • [ 604010-24-4 ]
YieldReaction ConditionsOperation in experiment
71.2% With palladium 10% on activated carbon; hydrogen In isopropyl alcohol at 20℃; for 48.00 h; [301] Step 2: tert-butyl 2, 6-dimethyl-4-oxopiperidine-l-carboxylate (0657) (0658) [302] To a stirred solution of l-benzyl-2,6-dimethylpiperidin-4-one (2 g, 9.17 mmol) in isopropyl alcohol (20 mL), 10percent Pd/C (400 mg) and Boc anhydride (2.39 g, 11 mmol) were added and stirred at room temperature under hydrogen pressure (balloon) for 48 h. The progress of the reaction was monitored by TLC. After completion, the mixture was filtered through a pad of celite, washed with 10percent MeOH/DCM, and filtrate was concentrated to yield a crude residue. The residue was purified by silica gel column chromatography eluting with 0-20percent ethyl acetate in n-hexane to afford the title compound as a white solid (1.5 g, yield 71.2percent). 1H NMR (400 (0659) MHz, chloroform-d) δ 4.41 - 4.33 (m, 2H), 2.85 (dd, / = 17.9, 6.5 Hz, 2H), 2.37 (dd, / = 17.8, 1.9 Hz, 2H), 1.49 (s, 9H), 1.25 (d, = 7.2 Hz, 6H).
Reference: [1] Patent: WO2016/196910, 2016, A1. Location in patent: Paragraph 301; 302
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  • [ 32941-09-6 ]
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Reference: [1] Patent: WO2015/103060, 2015, A1
[2] Patent: WO2016/203112, 2016, A1
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