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Chemical Structure| 1430230-57-1 Chemical Structure| 1430230-57-1

Structure of 1430230-57-1

Chemical Structure| 1430230-57-1

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Product Details of [ 1430230-57-1 ]

CAS No. :1430230-57-1
Formula : C6H13NO
M.W : 115.17
SMILES Code : O[C@@]1(C)[C@@H](N)CCC1

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Application In Synthesis of [ 1430230-57-1 ]

* 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 [ 1430230-57-1 ]

[ 1430230-57-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 796600-15-2 ]
  • [ 1430230-57-1 ]
  • 2-chloro-4-[[2-hydroxy-2-methylcyclopentyl]amino]-3-methylbenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With lithium carbonate; In water; dimethyl sulfoxide; at 130℃;Sealed tube; Example 22-Chloro-4-[[(lS,2R)-2-hydroxy-2-methyl-cyclopentyl]amino]-3-methyl-benzonitrilebsoluteIn a sealed pressure vessel, a mixture of <strong>[796600-15-2]2-chloro-4-fluoro-3-methyl-benzonitrile</strong> (1.2 g, 7.08 mmol), (lR,2S)-2-amino-l-methyl-cyclopentanol (1.63 g, 14.2 mmol) and lithium carbonate (1.10 g, 14.9 mmol) in DMSO (14.4 mL) and water (1.4 mL) is heated at 130 C overnight. After allowing the reaction to cool to room temperature, the mixture is diluted with EtOAc and washed twice with 1 N hydrochloric acid. The organic phase isconcentrated under reduced pressure and purified using radial chromatography eluting with EtOAc/hexanes (20 to 50% EtOAc/hexanes gradient). The resulting residue is repurified using radial chromatography with 1% methanol/dichloromethane. The isolated product is recrystallized with ether/hexanes, collected by filtration, and dried under reduced pressure to yield the title compound as a white solid (450 mg, 24%). A second crop (84 mg) is also isolated. LC-ES/MS m/z (35C1/37C1) 265/267 (M+l). 1H NMR (400 MHz, DMSO-d6) delta 1.16 (s, 3H), 1.71-1.73 (m, 5H), 2.12-2.13 (m, 1H), 2.14 (s, 3H), 3.46-3.50 (m, 1H), 4.93 (s, 1H), 5.26-5.30 (m, 1H), 6.63 (d, J= 8.8 Hz, 1H), 7.47 (d, J= 8.6 Hz, 1H). Chiral HPLC showed the material had an enantiomeric excess of 67%. The enantiomeric excess is determined by SFC on a CHIRALPAK AS-H (4.6 x 150 mm, 5 mupiiota) column using 20% ethanol/carbon dioxide. Flow rate: 5 mL/min. Detection: 225 nm. Isomer 1 (title compound):TR = 1.39 min; Isomer 2: TR = 1.99 min. The absolute stereochemistry of Isomer 1 (1S,2R) is known by correlation of retentions times with Isomer 1 and Isomer 2 as described inExample 3.The enantioenriched material (534 mg) is dissolved in methanol (5.5 mL) and purified in 500 mu?. injections by SFC on a CHIRALPAK AS-H (2.1 x 25 cm, 5 muiotaeta) column using 20% ethanol/carbon dioxide. Flow rate: 70 mL/min. Detection: 225 nm. The title compound is isolated as the first eluting peak, Isomer 1 (326 mg) in 99% enantiomeric excess. The enantiomeric excess is determined by SFC as described above.
 

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