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[ CAS No. 146552-71-8 ]

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2D
Chemical Structure| 146552-71-8
Chemical Structure| 146552-71-8
Structure of 146552-71-8 *Storage: {[proInfo.prStorage]}

Quality Control of [ 146552-71-8 ]

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Related Doc. of [ 146552-71-8 ]

SDS

Product Details of [ 146552-71-8 ]

CAS No. :146552-71-8MDL No. :MFCD08726031
Formula :C8H18N2O2Boiling Point :264°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :174.24Pubchem ID :15030821
Synonyms :

Computed Properties of [ 146552-71-8 ]

TPSA : 64.4 H-Bond Acceptor Count : 3
XLogP3 : 0.4 H-Bond Donor Count : 2
SP3 : 0.88 Rotatable Bond Count : 4

Safety of [ 146552-71-8 ]

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 [ 146552-71-8 ]

  • Upstream synthesis route of [ 146552-71-8 ]
  • Downstream synthetic route of [ 146552-71-8 ]

[ 146552-71-8 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 146610-69-7 ]
  • [ 146552-71-8 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen In methanol at 20℃; for 4.00 h; Pd/C(10percent, 2 g) was added to a solution of (S)-tert-butyl1-azidopropan-2-ylcarbamate (75.0 g, 0.375 mol) in MeOH (1 L). The suspensionwas stirred under a hydrogen atmosphere at r.t. for 4 h. The reaction was filteredand the solids washed with MeOH (100 mL). The combined filtrate was concentratedin vacuo to give (S)-tert-butyl1-aminopropan-2-ylcarbamate (65.1 g, quantitative yield), which was used innext step without further purification. 1H NMR (300 Hz, CDCl3)δ ppm 4.64 (br s, 1H), 3.64 (m, 1H), 2.75 (dd, J = 13.2, 5.1 Hz, 1H), 2.63 (dd, J = 13.2, 6.6 Hz, 1H), 1.45 (s, 9H), 1.31 (br s, 2H), 1.12 (d, J = 6.6Hz, 3H).
73% With hydrogen In ethyl acetate for 15.00 h; A stirred solution of 11.4 g (57 mmol) of 1c in 165 ml of ethyl acetate was mixed with 1.8 g of Pd/C (10percent) and exposed for 15 hours to a hydrogen atmosphere of 4 bar. The catalyst was separated by filtration (so-called G4 frit). The filtrate was concentrated by evaporation in a rotary evaporator and purified by column chromatography (SiO2-dichloromethane-->dichloromethane:methanol 1:1). The desired product was produced with a yield of 73percent (7.25 g; 42 mmol).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 24, p. 5743 - 5747
[2] Journal of Chemical Research, Miniprint, 1992, # 12, p. 3117 - 3132
[3] Patent: US2004/208828, 2004, A1. Location in patent: Page 13
[4] Organic Letters, 2011, vol. 13, # 13, p. 3486 - 3489
[5] Organic and Biomolecular Chemistry, 2013, vol. 11, # 17, p. 2780 - 2786
[6] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 16, p. 3157 - 3163
  • 2
  • [ 78981-25-6 ]
  • [ 146552-71-8 ]
YieldReaction ConditionsOperation in experiment
33% With borane-THF In tetrahydrofuran at 20 - 70℃; for 18.00 h; Inert atmosphere To a stirred solution of Boc-Ala-NH2 (4.600 g, 24.4 mmol, 1.0 equiv.) in anhydrous tetrahydrofuran (100 mL) under nitrogen was added 1.0 M borane-tetrahydrofuran complex in tetrahydrofuran (85.536 mL, 85.5 mmol, 3.5 equiv.). The mixture was stirred for 16 h at room temperature and then heated at 70° C. for 2 h. After cooling, the reaction was quenched with methanol until no bubbles generated. The mixture was heated at 70° C. for 2 h and then concentrated in vacuo. The residue was purified by silica gel column (0-100percent ethyl acetate/hexanes and then 0-30percent methanol/methylene chloride) to afford the desired product as a semi-solid (1.4 g, 33percent). 1H NMR (300 MHz, CDCl3): δ 4.60 (br s, 1H), 3.65 (m, 1H), 2.76 (dd, 1H, J=12.9, 4.8 Hz), 2.64 (dd, 1H, J=12.9, 6.6 Hz), 1.45 (s, 9H), 1.13 (d, 3H, J=6.9 Hz).
Reference: [1] Patent: US2015/284362, 2015, A1. Location in patent: Paragraph 0408
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 16, p. 4878 - 4881
[3] Journal of Combinatorial Chemistry, 2010, vol. 12, # 2, p. 248 - 254
[4] Patent: WO2016/206101, 2016, A1. Location in patent: Page/Page column 356
  • 3
  • [ 15967-72-3 ]
  • [ 121103-15-9 ]
  • [ 146552-71-8 ]
YieldReaction ConditionsOperation in experiment
36%
Stage #1: With triethylamine In ethanolHeating / reflux
Stage #2: With hydrogenchloride In water
Stage #3: With sodium hydroxide In water
A) (S)-2-Amino-propyl)-carbamic acid tert-butyl ester: To a solution of trietylamine (0.95 mL, 6.8 mmol) in 15 mL ethanol was added (s)-(-)- diaminopropane (252 mg, 74.1 mmol). The reaction mixture was stirred under reflux over night. Solvent was evaporated. Water was added and the pH was adjusted to pH 3 by addition of 2 M hydrochloric acid followed by extraction with dichloromethane. The aqueous phase was made alkaline by addition of 2 M sodium hydroxide and extracted with Q dichloromethane. The organic phase was dried over magnesium sulfate and dried in vacuo over night to give the sub-title compound (211 mg, 36 percent yield) and the by-product ((S)-2- amino-l-methyl-ethyl)-carbamic acid tert-butyl ester in a 3 : 1 mixture according to NMR.1H NMR (400 MHz; chloroform-d as solvent and internal reference) δ(ppm) 1.09 (d, 3H, / 5 = 6.5 Hz), 1.45 (s, 9H), 2.91 (m, IH), 3.04 (m, IH), 3.16 (m, IH)
36%
Stage #1: With triethylamine In ethanolHeating / reflux
Stage #2: With hydrogenchloride In water
A) ((S)-2-Amino-propyl)-carbamic acid tert-butyl ester: To a solution of trietylamine (0.95 mL, 6.8 mmol) in 15 mL ethanol was added (s)-(-)- diaminopropane (252 mg, 74.1 mmol). The reaction mixture was stirred under reflux over night. Solvent was evaporated. Water was added and the pH was adjusted to pH 3 by addition of 2 M hydrochloric acid followed by extraction with dichloromethane. The aqueous phase was made alkaline by addition of 2 M sodium hydroxide and extracted with dichloromethane. The organic phase was dried over magnesium sulfate and dried in vacuo over night to give the the sub-title compound (211 mg, 36 percent yield) and the by-product ((S)-2-amino-l-methyl-ethyl)-carbarnic acid tert-butyl ester in a 3 : 1 mixture according to NMR.1H NMR (400 MHz; chloroform-d as solvent and internal reference) δ(ppm) 1.09 (d, 3H, J = 6.5 Hz), 1.45 (s, 9H), 2.91 (m, IH), 3.04 (m, IH), 3.16 (m, IH)
Reference: [1] Patent: WO2007/8145, 2007, A1. Location in patent: Page/Page column 27
[2] Patent: WO2007/8144, 2007, A1. Location in patent: Page/Page column 17; 23-24
  • 4
  • [ 79069-13-9 ]
  • [ 146552-71-8 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1992, # 12, p. 3117 - 3132
[2] Organic Letters, 2011, vol. 13, # 13, p. 3486 - 3489
[3] Bioscience, Biotechnology and Biochemistry, 2011, vol. 75, # 4, p. 780 - 782
[4] Patent: WO2011/161216, 2011, A1
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 8, p. 2877 - 2879
[6] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 21, p. 6305 - 6312,8
[7] Patent: US2013/210818, 2013, A1
[8] Patent: US2015/141323, 2015, A1
[9] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 16, p. 3157 - 3163
[10] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 24, p. 5743 - 5747
[11] Patent: WO2009/115572, 2009, A2
  • 5
  • [ 126301-16-4 ]
  • [ 146552-71-8 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1992, # 12, p. 3117 - 3132
[2] Organic Letters, 2011, vol. 13, # 13, p. 3486 - 3489
[3] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 24, p. 5743 - 5747
  • 6
  • [ 24424-99-5 ]
  • [ 146552-71-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 8, p. 2877 - 2879
[2] Patent: WO2016/206101, 2016, A1
  • 7
  • [ 109208-68-6 ]
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Reference: [1] Patent: US2015/141323, 2015, A1
  • 8
  • [ 15761-38-3 ]
  • [ 146552-71-8 ]
Reference: [1] Patent: US2015/141323, 2015, A1
  • 9
  • [ 28875-17-4 ]
  • [ 146552-71-8 ]
Reference: [1] Patent: US2015/284362, 2015, A1
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