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Chemical Structure| 335592-60-4 Chemical Structure| 335592-60-4

Structure of 335592-60-4

Chemical Structure| 335592-60-4

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Product Details of [ 335592-60-4 ]

CAS No. :335592-60-4
Formula : C20H32BNO4
M.W : 361.28
SMILES Code : O=C(OC(C)(C)C)NC(C)(C1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1)C
MDL No. :MFCD22494620

Safety of [ 335592-60-4 ]

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

Application In Synthesis of [ 335592-60-4 ]

* 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 [ 335592-60-4 ]

[ 335592-60-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 214973-83-8 ]
  • [ 73183-34-3 ]
  • [ 335592-60-4 ]
YieldReaction ConditionsOperation in experiment
84% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 80℃; for 5h; Step 4: Preparation of tert-butyl {1-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl}carbamate A suspension of tert-butyl[1-(4-bromophenyl)-1-methylethyl]carbamate (500 mg) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane (485 mg) and potassium acetate (468 mg) and PdCl2(dppf)CH2Cl2 (39 mg) in dimethylsulfoxide (8 mL) was degassed for 5 min. then stirred at 80 C. for 5 h. The reaction mixture was diluted with benzene and filtered. The filtrate was washed with brine (5 times). The organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (0-15% ethyl acetate in hexanes) gave the product (481 mg, 84%). 1HNMR (CDCl3) 400 MHz delta: 7.77 (d, J=8.3 Hz, 2H), 7.40 (d, J=8.3 Hz, 2H), 4.95 (br s, 1H), 1.61 (br s, 6H), 1.46-1.07 (m, 9H), 1.33 (s, 12H).
5.67 g With potassium acetate; palladium diacetate; XPhos; In acetonitrile; at 75℃; for 18h;Inert atmosphere; Step 2: tert-butyl (2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)propan-2- yl)carbamate: The product from Step 1 above (6 g, 18.52 mmol, 97% purity), bis- (pinacolato)diboron (5.82 g, 22.91 mmol), palladium(II) acetate (0.107 g, 0.477 mmol), potassium acetate (5.62 g, 57.3 mmol) and XPhos (0.457 g, 0.955 mmol) were combined in MeCN (50 ml). The vessel was purged with N2 then heated at 75 C for 18 h. The reaction mixture was cooled, filtered through Celite, washing with MeCN (2 x 50 ml), and concentrated in vacuo to afford a brown oil. The residue was partitioned between DCM (50 ml) and water (50 ml). The phases were separated and the organic phase was concentrated in vacuo to afford a brown soild. The crude product was purified by columnchromatography (220 g cartridge, 0-20% EtOAc/isohexane) to afford the title compound (5.67 g, 15.1 mmol, 96% purity) as an off-white solid. LCMS (Method 1): m/z 306 (M+H- C4H8)+ at 2.83 min.
  • 2
  • [ 214973-83-8 ]
  • [ 61676-62-8 ]
  • [ 335592-60-4 ]
YieldReaction ConditionsOperation in experiment
58% (Referential Example 6) Synthesis of 4-(1-tert-butoxycarbonylamino-1-methylethyl)-1-(4,4,5,5-tetramethyl[1,3,2]dioxaborolanyl)benzene (referential compound 6-1) A 0.95M sec-butyl lithium/n-hexane solution (370 ml, 350 mmol) was dropped, in an argon stream with stirring at -78C, into a solution of 50 g (160 mmol) of <strong>[214973-83-8]1-bromo-4-(1-tert-butoxycarbonylamino-1-methylethyl)benzene</strong>(referential compound 4-1) in 800 ml of diethyl ether and the mixture was stirred for 30 minutes. After that, 97 ml (480 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane was dropped thereinto at -78C and the mixture was stirred at -50C for 2 hours. After the reaction was finished, 300 g of a saturated aqueous solution of ammonium chloride and then 450 ml of water were successively added thereto and the mixture was separated into layers. An aqueous layer was extracted with 300 ml of ethyl acetate again and the organic layers were combined, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated in vacuo. n-Hexane (100 ml) was added to the resulting residue and the resulting solid was filtered off and successively washed with 100 ml of a mixed solvent (n-hexane: ethyl acetate = 4:1 (v/v)) and 100 ml of n-hexane to give 33 g of the title compound as white powder (yield: 58%). Melting point: 142 to 144C Rf value: 0.38 (n-hexane: ethyl acetate = 4:1 (v/v)) Mass spectrum (CI, m/z): 362 (M+ + 1) 1H-NMR spectrum (CDCl3, delta ppm): 1.10-1.50 (m, 21H), 1.61 (s, 6H), 4.93 (brs, 1H), 7.37-7.42 (m, 2H), 7.74-7.79 (m, 2H)
58% 370 ml (350 mmol) of a 0.95 M sec-butyl lithium/n-hexane solution was added dropwise to a solution of 50 g (160 mmol) of <strong>[214973-83-8]1-bromo-4-(1-tert-butoxycarbonylamino-1-methylethyl)benzene</strong> (Reference Compound 4-1) in 800 ml of diethyl ether at -78 C. in an argon stream with stirring, and the mixture was stirred for 30 minutes. Then, 97 ml (480 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane was added dropwise thereto at -78 C. and the mixture was stirred at -50 C. for 2 hours. After the reaction was completed, 300 g of a saturated aqueous solution of ammonium chloride was added to the resulting solution, and 450 ml of water was poured into the solution to separate the mixture into layers. An aqueous layer was extracted with 300 ml of ethyl acetate again and the organic layers were combined, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. 100 ml of n-hexane was added to the resulting residue and the resulting solid was collected by filtration and successively washed with 100 ml of a mixed solvent (n-hexane:ethyl acetate=4:1 (v/v)) and 100 ml of n-hexane, whereby 33 g of the title compound was obtained as white powder (yield: 58%). Melting point: 142 to 144 C. Rf value: 0.38 (n-hexane:ethyl acetate=4:1 (v/v)) Mass spectrum (CI, m/z): 362 (M++1) 1H-NMR spectrum (CDCl3, deltappm): 1.10-1.50 (m, 21H), 1.61 (s, 6H), 4.93 (brs, 1H), 7.37-7.42 (m, 2H), 7.74-7.79 (m, 2H)
58% (Reference Example 5) Synthesis of 4-(1-tert-butoxycarbonylamino-1-methylethyl)-1-(4,4,5,5-tetramethyl[1,3,2]dioxaborolanyl)benzene (Reference compound 5) 370 ml (350 mmol) of a 0.95 M sec-butyl lithium/ n-hexane solution was added dropwise to a solution of 50 g (160 mmol) of <strong>[214973-83-8]1-bromo-4-(1-tert-butoxycarbonylamino-1-methylethyl)benzene</strong> (Reference compound 4-1) in 800 ml of diethyl ether at -78C in an argon stream with stirring, and the mixture was stirred for 30 minutes. Then, 97 ml (480 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl[1,3,2] dioxaborolane was added dropwise thereto at -78C and the mixture was stirred at -50C for 2 hours. After the reaction was completed, 300 g of a saturated aqueous solution of ammonium chloride was added to the resulting solution, and 450 ml of water was poured into the solution to separate the mixture into layers. An aqueous layer was extracted with 300 ml of ethyl acetate again and the organic layers were combined, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. 100 ml of n-hexane was added to the resulting residue and the resulting solid was collected by filtration and successively washed with 100 ml of a mixed solvent (n-hexane: ethyl acetate = 4: 1 (v/v)) and 100 ml of n-hexane, whereby 33 g of the title compound was obtained as white powder (yield: 58%). Melting point: 142 to 144C Rf value: 0.38 (n-hexane: ethyl acetate = 4: 1 (v/v)) Mass spectrum (CI, m/z): 362 (M++1) 1H-NMR spectrum (CDCl3, deltappm): 1.10-1.50 (m, 21H), 1.61 (s, 6H), 4.93 (brs, 1H), 7.37-7.42 (m, 2H), 7.74-7.79 (m, 2H)
  • 3
  • [ 214973-83-8 ]
  • [1,1'-bis(di-phenylphosphino)ferrocene]dichloropalladium [ No CAS ]
  • [ 73183-34-3 ]
  • [ 335592-60-4 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate; In dichloromethane; N,N-dimethyl-formamide; A mixture of <strong>[214973-83-8]tert-butyl N-{1-(4-bromophenyl)-1-methylethyl}carbamate</strong> (1.57 g, 5.0 mmol), bis(pinacolato)diboron (1.40 g, 5.5 mmol), [1,1'-bis(di-phenylphosphino)ferrocene]dichloropalladium(II) (123 mg, 0.015 mmol) and potassium acetate (1.47 g, 15.0 mmol) was dissolved in dry DMF (20 ml) under nitrogen and heated to 80 for 5 h. The reaction was then concentrated under reduced pressure, the resulting residue taken up in dichloromethane (80 ml) and washed with water (1*80 ml), then brine (1*80 ml), dried (MgSO4) and again concentrated. The residue was subjected to column chromatography (silica gel; 15% ethyl acetate-hexane) to give tert-butyl N-{1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1-methylethyl}carbamate (1.55 g) as a white solid m.p. 140. deltaH (CDCl3) 7.77 (2H, d, J 8.3 Hz), 7.40 (2H, d, J 8.4 Hz), 1.63 (6H, s) and 1.34 (21H, s).
 

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