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Chemical Structure| 168827-91-6 Chemical Structure| 168827-91-6

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Chemical Structure| 168827-91-6

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Product Details of [ 168827-91-6 ]

CAS No. :168827-91-6
Formula : C12H17NO3
M.W : 223.27
SMILES Code : O=C(OCC1=CC=CC=C1)N[C@@H](C)CCO
MDL No. :MFCD27956455

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Application In Synthesis of [ 168827-91-6 ]

* 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 [ 168827-91-6 ]

[ 168827-91-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 168827-91-6 ]
  • [ 61477-39-2 ]
YieldReaction ConditionsOperation in experiment
92% With palladium on activated charcoal; hydrogen; In methanol; at 25℃; for 12h; Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(25)-4-hydroxybutan-2- yljcarbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25°C for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (3S)-3-aminobutan-l-ol as an oil. 1H NMR (300MHz, OMSO, ppm): delta 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), m/z, 90 [M+H] +; measured [a]D2a2 +11.65° (C=1.22g/100mL in EtOH), lit. [a]D2° +16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61, 2293-2304.).
92% With palladium on activated charcoal; hydrogen; In methanol; at 25℃; for 12h; Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(2S)-4-hydroxybutan-2- yllcarbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25°C for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g(92percent) of (3S)-3-aminobutan-1-ol as an oil. ?H NMR (300MHz, DMSO, ppm): oe 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), mlz, 90 [M+Hj measured [cL1D202 +11.650 (C=1.22gIlOOmL in EtOH), lit. [ctlD2° +16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61, 2293?2304.).Using the above procedure, 12.0 g 12 g (94percent) of (3R)-3-aminobutan-1-ol was isolated as an oil. ?H NMR (300MHz, DMSO, ppm): oe 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), mz, 90 [M+Hj measured [ct1D202 -11.1° (C = 0.32g/lOOmL in EtOH), lit. [ct1D25 -25° (c=1.25 in EtOH) (Tetrahedron: Asymmetry 1999, 10, 2213?2224.).
92% With palladium on activated charcoal; hydrogen; In methanol; at 25℃; for 12h; Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(2S)-4-hydroxybutan-2-yl]carbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25° C. for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (3S)-3-aminobutan-1-ol as an oil. 1H NMR (300 MHz, DMSO, ppm): delta 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), m/z, 90 [M+H]+; measured [alpha]D20.2+11.65° (C=1.22 g/100 mL in EtOH), lit. [alpha]D20+16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61, 2293-2304.).
92% With palladium on activated charcoal; hydrogen; In methanol; at 25℃; for 12h; Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(2S)-4-hydroxybutan-2-yl]carbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25° C. for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (3S)-3-aminobutan-1-ol as an oil. 1H NMR (300 MHz, DMSO, ppm): delta 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), m/z, 90 [M+H]+; measured [alpha]D20.2+11.65° (C=1.22 g/100 mL in EtOH), lit. [alpha]D20+16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61, 2293 2304.).
92% With palladium on activated charcoal; hydrogen; In methanol; at 25℃; for 12h; Step 3: (3R)-3-Aminobutan-l-ol and (3y)-3-Aminobutan-l-ol Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(2S)-4- hydroxybutan-2-yl]carbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25°C for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (35)-3-aminobutan-l-ol as an oil. *H NMR (300MHz, DMSO, ppm): delta 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), m/z, 90 [M+H] +; measured [a]D20 2 +11.65° (C=1.22g/100mL in EtOH), lit. [a]D20 +16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61 , 2293- 2304.). Using the above procedure, 12.0 g 12 g (94percent) of (3R)-3-aminobutan-l-ol was isolated as an oil. lU NMR (300MHz, DMSO, ppm): delta 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), m/z, 90 [M+H] +; measured [a]D20 2 -11.1° (C = 0.32g/100mL in EtOH), lit. [a]D25 -25° (c= 1.25 in EtOH) (Tetrahedron: Asymmetry 1999, 10, 2213-2224).
92% With palladium on activated charcoal; hydrogen; In methanol; at 25℃; for 12h; Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(2S)-4-hydroxybutan-2-yllcarbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) andpalladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25°C for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (3S)-3-aminobutan-1-ol as an oil. ?H NMR (300MHz, DMSO, ppm): oe 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS(ESI), mlz, 90 [M+Hj measured [cL1D202 +11.65° (C=1.22gIlOOmL in EtOH), lit. [ctlD2° +16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61, 2293?2304.).
92% With palladium on activated charcoal; hydrogen; In methanol; at 25℃; for 12h; Into a 1000-mL round-bottom flask was placed a solution of benzyl A^-[(25')-4-hydroxybutan-2- yl]carbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25°C for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (3S)-3- aminobutan-l-ol as an oil. NMR (300MHz, DMSO, ppm): delta 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), m/z, 90 [M+H] +; measured [a]D20 2 +11.65° (C=1.22g/100mL in EtOH), lit. [a]D20 +16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 61 , 2293-2304.).
92% With palladium 10% on activated carbon; hydrogen; In methanol; at 25℃; for 12h; Into a 1000-mL round-bottom flask was placed a solution of benzyl N-[(2S)-4-hydroxybutan-2-yl]carbamate (30 g, 134.4 mmol, 1.00 equiv) in methanol (500 mL) and palladium carbon (3 g, 0.10 equiv). The resulting solution was stirred at 25°C for 12 h under an atmosphere of hydrogen. The solids were filtered out and the filtrate was concentrated under vacuum to afford 11.7 g (92percent) of (3S)-3-aminobutan-1-ol as an oil. 1H NMR (300MHz, DMSO, ppm): delta 4.48 (3H, s), 3.47 (2H, s), 2.96 (1H, s), 1.47-1.41 (2H, q), 1.02-0.99 (3H, d); LCMS (ESI), mlz, 90 [M+H] measured [alpha]D20.2° +11.65° (C=1.22g/l00mL in EtOH), lit. [alpha]D20° +16.3° (c=4.5 in EtOH) (J. Org. Chem. 1996, 6], 2293?2304.).

  • 2
  • [ 61477-39-2 ]
  • [ 501-53-1 ]
  • [ 168827-91-6 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In water; The purity was measured directly by gas chromatography. Ee assay: 3-aminobutanol was first reacted with benzyloxycarbonyl chloride in aqueous sodium hydroxide to form N-Cbc-3-aminobutanol and then detected by liquid phase. Column AD-H; Flowable n-hexane: isopropanol (9: 1); flow rate, 1 ml / min. Detection wavelength, 210 nm. Retention time, S-isomer, 11.1 min, R-isomer 12.2 min.
 

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