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[ CAS No. 167216-17-3 ]

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2D
Chemical Structure| 167216-17-3
Chemical Structure| 167216-17-3
Structure of 167216-17-3 *Storage: {[proInfo.prStorage]}

Quality Control of [ 167216-17-3 ]

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Product Details of [ 167216-17-3 ]

CAS No. :167216-17-3MDL No. :MFCD18831346
Formula : C9H19NO3 Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :189.25Pubchem ID :-
Synonyms :

Computed Properties of [ 167216-17-3 ]

TPSA : 58.6 H-Bond Acceptor Count : 3
XLogP3 : 1 H-Bond Donor Count : 2
SP3 : 0.89 Rotatable Bond Count : 5

Safety of [ 167216-17-3 ]

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 [ 167216-17-3 ]

  • Upstream synthesis route of [ 167216-17-3 ]

[ 167216-17-3 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 159877-47-1 ]
  • [ 167216-17-3 ]
YieldReaction ConditionsOperation in experiment
1.3 g
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at -78℃; for 1.00 h; Inert atmosphere
Stage #2: With sodium hydroxide In water at 20℃; for 1.00 h;
To a solution of (R)-3-((tert-butoxycarbonyl)amino)butanoate (3.0 g, 14.76 mmol) in tetrahydrofuran (THF) (50 mL) was added aluminum(III) lithium hydride (0.728 g, 19.19 mmol), stirred at -78 °C for 1 h under nitrogen. The reaction mixture was warmed to 0°C, quenched by addition of H20 (0.7 mL) and aq. 15percent NaOH (0.7 mL), stirred for 1 h at r.t, filtered through celite, dried over Na2S04, concentrated to afford the title compound (1.3 g).
Reference: [1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 1, p. 92 - 96
[2] Patent: US2011/237814, 2011, A1. Location in patent: Page/Page column 11
[3] Patent: WO2014/114249, 2014, A1. Location in patent: Page/Page column 21
  • 2
  • [ 159991-23-8 ]
  • [ 167216-17-3 ]
YieldReaction ConditionsOperation in experiment
95% With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at -20℃; Green chemistry 100 g of N-Boc-(R)-3-aminobutyric acid and 300 mL of tetrahydrofuran were placed in a reaction flask, 20.6 g of sodium borohydride was added in portions, the temperature was lowered to -20 °C, and 100 g of boron trifluoride etherate was slowly added dropwise. HPLC to determine whether the raw material reaction is complete. After completion of the reaction, the reaction was quenched by the addition of methanol, and the solvent was evaporated. Filter to remove solids,The filtrate was washed with 100 ml of saturated sodium bicarbonate.The organic phase was concentrated to give N-Boc-(R)-3-aminobutanol as a white solid, 88 g, yield 95percent, mp. 99.0percent (HPLC method).
91% With sodium tetrahydroborate; iodine In tetrahydrofuran at 0 - 30℃; 115 g of the compound of formula I was dissolved in 460 mL of tetrahydrofuran, cooled to 0~10 ° C. in an ice bath, 23.7 g of sodium borohydride was added in portions, the temperature was controlled at 0~10 ° C., and 165.4 g of elemental iodine Of 230 mL of tetrahydrofuran solution, the dropwise addition, and gradually warmed to 25 ~ 30 ° C,Liquid phase tracking is complete until the conversion of the raw material, 60 mL of water is added dropwise to quench the reaction, concentrated under reduced pressure to no distillate, 500 mL of methanol is added, the temperature is raised to 55-60 ° C., the solution is incubated for 0.5 h, mL water, drops After completion of the incubation, the mixture was stirred for 1 hour, then slowly cooled to 15-20 ° C, filtered and dried to obtain 97.4 g of the compound of formula II in a yield of 91percent.
Reference: [1] Patent: CN108424370, 2018, A. Location in patent: Paragraph 0090; 0091
[2] Patent: CN106966912, 2017, A. Location in patent: Paragraph 0022; 0023; 0024
  • 3
  • [ 24424-99-5 ]
  • [ 61477-40-5 ]
  • [ 167216-17-3 ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine In dichloromethane at 20 - 24℃; for 4.00 h; Example 36
Preparation of (R)-tert-butyl(4-hydroxybutan-2-yl)carbamate (C56)
Triethylamine (2.35 mL, 16.8 mmol) and di-tert-butyl dicarbonate (2.50 g, 12.3 mmol) were added to a solution of (R)-3-aminobutan-1-ol (1.00 g, 11.2 mmol) in dichloromethane (10 mL).
The reaction mixture was stirred for 4 hours at room temperature.
The reaction mixture was concentrated, the residue poured into ice water, and then extracted with ethyl acetate.
The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated.
Purification by flash column chromatography using 20percent ethyl acetate/petroleum ether as eluent provided the title compound as a white solid (1.7 g, 80percent): 1H NMR (400 MHz, DMSO-d6) δ 6.62 (d, J=8.4 Hz, 1H), 4.43-4.31 (m, 1H), 3.55-3.52 (m, 1H), 3.40-3.38 (m, 2H), 1.55-1.48 (m, 2H), 1.43 (s, 9H), 1.01 (d, J=6.8 Hz, 3H).
Reference: [1] Patent: US2017/210723, 2017, A1. Location in patent: Paragraph 0537-0538
  • 4
  • [ 161529-22-2 ]
  • [ 167216-17-3 ]
Reference: [1] Patent: WO2005/26113, 2005, A1. Location in patent: Page 32-33
  • 5
  • [ 1047665-48-4 ]
  • [ 167216-17-3 ]
Reference: [1] Chemistry - A European Journal, 2009, vol. 15, # 9, p. 2050 - 2054
[2] Chemistry - A European Journal, 2009, vol. 15, # 40, p. 10514 - 10532
  • 6
  • [ 24424-99-5 ]
  • [ 167216-17-3 ]
Reference: [1] Patent: WO2014/114249, 2014, A1
  • 7
  • [ 159877-47-1 ]
  • [ 167216-17-3 ]
YieldReaction ConditionsOperation in experiment
1.3 g
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at -78℃; for 1.00 h; Inert atmosphere
Stage #2: With sodium hydroxide In water at 20℃; for 1.00 h;
To a solution of (R)-3-((tert-butoxycarbonyl)amino)butanoate (3.0 g, 14.76 mmol) in tetrahydrofuran (THF) (50 mL) was added aluminum(III) lithium hydride (0.728 g, 19.19 mmol), stirred at -78 °C for 1 h under nitrogen. The reaction mixture was warmed to 0°C, quenched by addition of H20 (0.7 mL) and aq. 15percent NaOH (0.7 mL), stirred for 1 h at r.t, filtered through celite, dried over Na2S04, concentrated to afford the title compound (1.3 g).
Reference: [1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 1, p. 92 - 96
[2] Patent: US2011/237814, 2011, A1. Location in patent: Page/Page column 11
[3] Patent: WO2014/114249, 2014, A1. Location in patent: Page/Page column 21
  • 8
  • [ 159991-23-8 ]
  • [ 167216-17-3 ]
YieldReaction ConditionsOperation in experiment
95% With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at -20℃; Green chemistry 100 g of N-Boc-(R)-3-aminobutyric acid and 300 mL of tetrahydrofuran were placed in a reaction flask, 20.6 g of sodium borohydride was added in portions, the temperature was lowered to -20 °C, and 100 g of boron trifluoride etherate was slowly added dropwise. HPLC to determine whether the raw material reaction is complete. After completion of the reaction, the reaction was quenched by the addition of methanol, and the solvent was evaporated. Filter to remove solids,The filtrate was washed with 100 ml of saturated sodium bicarbonate.The organic phase was concentrated to give N-Boc-(R)-3-aminobutanol as a white solid, 88 g, yield 95percent, mp. 99.0percent (HPLC method).
91% With sodium tetrahydroborate; iodine In tetrahydrofuran at 0 - 30℃; 115 g of the compound of formula I was dissolved in 460 mL of tetrahydrofuran, cooled to 0~10 ° C. in an ice bath, 23.7 g of sodium borohydride was added in portions, the temperature was controlled at 0~10 ° C., and 165.4 g of elemental iodine Of 230 mL of tetrahydrofuran solution, the dropwise addition, and gradually warmed to 25 ~ 30 ° C,Liquid phase tracking is complete until the conversion of the raw material, 60 mL of water is added dropwise to quench the reaction, concentrated under reduced pressure to no distillate, 500 mL of methanol is added, the temperature is raised to 55-60 ° C., the solution is incubated for 0.5 h, mL water, drops After completion of the incubation, the mixture was stirred for 1 hour, then slowly cooled to 15-20 ° C, filtered and dried to obtain 97.4 g of the compound of formula II in a yield of 91percent.
Reference: [1] Patent: CN108424370, 2018, A. Location in patent: Paragraph 0090; 0091
[2] Patent: CN106966912, 2017, A. Location in patent: Paragraph 0022; 0023; 0024
  • 9
  • [ 24424-99-5 ]
  • [ 61477-40-5 ]
  • [ 167216-17-3 ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine In dichloromethane at 20 - 24℃; for 4.00 h; Example 36
Preparation of (R)-tert-butyl(4-hydroxybutan-2-yl)carbamate (C56)
Triethylamine (2.35 mL, 16.8 mmol) and di-tert-butyl dicarbonate (2.50 g, 12.3 mmol) were added to a solution of (R)-3-aminobutan-1-ol (1.00 g, 11.2 mmol) in dichloromethane (10 mL).
The reaction mixture was stirred for 4 hours at room temperature.
The reaction mixture was concentrated, the residue poured into ice water, and then extracted with ethyl acetate.
The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated.
Purification by flash column chromatography using 20percent ethyl acetate/petroleum ether as eluent provided the title compound as a white solid (1.7 g, 80percent): 1H NMR (400 MHz, DMSO-d6) δ 6.62 (d, J=8.4 Hz, 1H), 4.43-4.31 (m, 1H), 3.55-3.52 (m, 1H), 3.40-3.38 (m, 2H), 1.55-1.48 (m, 2H), 1.43 (s, 9H), 1.01 (d, J=6.8 Hz, 3H).
Reference: [1] Patent: US2017/210723, 2017, A1. Location in patent: Paragraph 0537-0538
  • 10
  • [ 161529-22-2 ]
  • [ 167216-17-3 ]
Reference: [1] Patent: WO2005/26113, 2005, A1. Location in patent: Page 32-33
  • 11
  • [ 1047665-48-4 ]
  • [ 167216-17-3 ]
Reference: [1] Chemistry - A European Journal, 2009, vol. 15, # 9, p. 2050 - 2054
[2] Chemistry - A European Journal, 2009, vol. 15, # 40, p. 10514 - 10532
  • 12
  • [ 24424-99-5 ]
  • [ 167216-17-3 ]
Reference: [1] Patent: WO2014/114249, 2014, A1
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