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[ CAS No. 131852-53-4 ] {[proInfo.proName]}

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Chemical Structure| 131852-53-4
Chemical Structure| 131852-53-4
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Product Details of [ 131852-53-4 ]

CAS No. :131852-53-4 MDL No. :MFCD06762908
Formula : C16H24N2O2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :PHOIDJGLYWEUEK-AWEZNQCLSA-N
M.W : 276.37 Pubchem ID :10850083
Synonyms :

Safety of [ 131852-53-4 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338-P310 UN#:
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 131852-53-4 ]

* 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.

  • Upstream synthesis route of [ 131852-53-4 ]
  • Downstream synthetic route of [ 131852-53-4 ]

[ 131852-53-4 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 24424-99-5 ]
  • [ 114715-38-7 ]
  • [ 131852-53-4 ]
YieldReaction ConditionsOperation in experiment
94.1%
Stage #1: With sodium hydroxide In water at 50 - 60℃;
Stage #2: for 3 h; 		A 500 ml four-neck flask equipped with a stirrer, a thermometer, a Dimroth condenser, and a titration funnel was loaded with (S)-3-amino-1-benzylpyrrolidine 17.6 g (0.1 mole, optical purity 99.5percent/ee), water 158.7 g, and Cation DS (manufactured by Sanyo Chemical Industries, Ltd.) 0.2 g and the pH of the mixture was adjusted to be 11+/-0.5 with an aqueous 48percent sodium hydroxide solution. While the mixture being stirred at 50 to 60°C, di-tert-butyl dicarbonate (hereinafter abbreviated as DiBoc) 26.2 g (0.12 mole) was dropwise added for about 2 hours. During the time, the reaction solution was adjusted at pH 11+/-0.5 with an aqueous 48percent sodium hydroxide solution. After being stirred for further 1 hour, the reaction solution was cooled to a room temperature and precipitated crystal was separated by filtration. The crystal was vacuum dried at 50°C to obtain (S)-1-benzyl-3-tert-butoxycarbonylaminopyrrolidine 26.0 g. The yield was 94.1percent and the chemical purity was 99.1 percent and an optical purity was 99.5percent ee. The same apparatus as that of Example 1 was loaded with (S)-1-benzyl-3-tert-butoxycarbonylaminopyrrolidine 26.0 g (optical purity 99.5percent ee), water 120 g, and 5percent Pd/C 2.6 g (PE type, 55.27percent water content, manufactured by N. E. Chemcat Corp.) and the contents were stirred at reaction temperature of 40°C for 10 hours under hydrogen ventilation. When the reaction solution was analyzed by GC, and the peak of the raw material disappeared and other than toluene only 3-tert-butoxycarbonylaminopyrrolidine was detected. After completion of the reaction, Pd/C was removed by filtration and the filtrate was concentrated to 30 g by an evaporator. Next, the concentrated product was mixed with toluene and concentrated to 20 g to remove water by azeotropic boiling. While being mixed, the concentrated solution was mixed slowly with n-hexane 25 g to precipitate a crystal and further stirred for 2 hour in an ice bath. The precipitated crystal was separated by filtration and vacuum dried to obtain (S)-3-tert-butoxycarbonylaminopyrrolidine 15.4 g. The yield was 87.4percent, the chemical purity was 99.5 areapercent, and an optical purity was 99.5 percent ee. The water content was 0.4percent.
Reference： [1] Patent: EP1640364, 2006, A1, . Location in patent: Page/Page column 10-11
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 11, p. 1815 - 1826
  • 2
  • [ 100-52-7 ]
  • [ 122536-76-9 ]
  • [ 131852-53-4 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #1: at 20℃; for 0.166667 h;
Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane; N,N-dimethyl-formamide at 20℃; for 5 h; 		EXAMPLE 67 Synthesis of (S)-4-((1-benzylpyrrolidin-3-yl)amino)-3-chloro-/V-(1 ,2,4-thiadiazol-5- yl)benzenesulfonamide 2,2,2-trifluoroacetate Step 1. Preparation of te/f-butyl (S)-(1-benzylpyrrolidin-3-yl)carbamate To a solution of terf-butyl (S)-pyrrolidin-3-ylcarbamate (0.30 g, 1.60 mmol) in anhydrous 1 ,2-dichloroethane (2 mL) and anhydrous A/,A/-dimethylformamide (2 mL) was added benzaldehyde (0.26 g, 2.40 mmol). The reaction mixture was stirred at ambient temperature for 10 minutes and then sodium triacetoxyborohydride (0.68 g, 3.20 mmol) was added to it. The reaction mixture was stirred at ambient temperature for 5 h. After dilution with ethyl acetate (50 mL), the mixture was washed with brine (3 x 50 mL), dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate in vacuo provided the title compound as colorless oil (0.37 g, 84 percent yield). H NMR (300 MHz, CDCI3) 7.58-7.53 (m, 2H), 7.46-7.39 (m, 3H), 4.55-4.49 (m, 1 H), 4.16 (s, 2H), 3.67-3.52 (m, 1 H), 3.40-3.36 (m, 1 H), 3.12-3.06 (m, 1 H), 2.91-2.81 (m, 1 H), 2.52-2.40 (m, 1 H), 2.25-2.12 (m, 1 H), 1.39 (s, 9H), NH not observed; MS (ES+) m/z 277.2 (M + 1).
Reference： [1] Patent: WO2017/201468, 2017, A1, . Location in patent: Page/Page column 180-181
  • 3
  • [ 101385-90-4 ]
  • [ 131852-53-4 ]
Reference： [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 11, p. 1815 - 1826
  • 4
  • [ 114636-29-2 ]
  • [ 131852-53-4 ]
Reference： [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 11, p. 1815 - 1826
  • 5
  • [ 114715-35-4 ]
  • [ 131852-53-4 ]
Reference： [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 11, p. 1815 - 1826
  • 6
  • [ 130622-08-1 ]
  • [ 131852-53-4 ]
Reference： [1] Synthetic Communications, 1998, vol. 28, # 21, p. 3919 - 3926
  • 7
  • [ 128427-10-1 ]
  • [ 131852-53-4 ]
Reference： [1] Synthetic Communications, 1998, vol. 28, # 21, p. 3919 - 3926
  • 8
  • [ 100-46-9 ]
  • [ 176970-13-1 ]
  • [ 131852-53-4 ]
Reference： [1] Synthetic Communications, 1998, vol. 28, # 21, p. 3919 - 3926
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