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Chemical Structure| 20412-66-2 Chemical Structure| 20412-66-2

Structure of 20412-66-2

Chemical Structure| 20412-66-2

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Product Details of [ 20412-66-2 ]

CAS No. :20412-66-2
Formula : C6H13NO
M.W : 115.17
SMILES Code : OC1(C)C(N)CCC1
MDL No. :MFCD19203255

Safety of [ 20412-66-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H315-H318-H335-H227
Precautionary Statements:P210-P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P332+P313-P362-P370+P378-P403+P233-P403+P235-P405-P501
Class:8
UN#:2735
Packing Group:

Application In Synthesis of [ 20412-66-2 ]

* 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 [ 20412-66-2 ]

[ 20412-66-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 796600-15-2 ]
  • [ 20412-66-2 ]
  • 2-chloro-4-[[2-hydroxy-2-methylcyclopentyl]amino]-3-methylbenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With lithium carbonate; In water; dimethyl sulfoxide; at 130℃; for 36h;Sealed tube; Inert atmosphere; Example 1tra/?s-2-Chloro-4-[ [2-hydroxy-2-methyl-cyclopentyl] amino] -3 -methyl-benzonitrile, Isomer 2bsoluteIn a glass pressure vessel, a mixture of trans-2-amino-l-methyl-cyclopentanol (8.75 g, 53 mmol, 1.5 eq), <strong>[796600-15-2]2-chloro-4-fluoro-3-methyl-benzonitrile</strong> (6 g, 35.4 mmol) and lithium carbonate (7.84 g, 106 mmol) in DMSO (72 mL) and water (7.2 mL) is degassed for 15 min by bubbling nitrogen through the mixture. The vessel is sealed and heated at 130 C for 36 h. After cooling to room temperature, the mixture is quenched over ice/water (700 mL) at 5 C (internal temperature) with stirring. After 15 min, the initially sticky solid turns into a cream solid that is collected by filtration and washed with cold water. The solid is stirred over EtOAc (100 mL) for 30 min and filtered through a pad of diatomaceous earth. The EtOAc filtrate is concentrated to afford 15 g of a yellow solid. The material is purified by silica gel chromatography using dichloromethane to elute impurities and 10%EtOAc/dichloromethane to elute final product to obtain the racemic title compound (9.2 g, 98%). 1H NMR (400 MHz, DMSO-d6) delta 7.48 (d, 1H), 6.90 (d, 1H), 5.51 (d, 1H), 4.66 (s, 1H), 3.65-3.74 (m, 1H), 2.21 (s, 3H), 2.01-2.13 (m, 1H), 1.50-1.78 (m, 5H), 1.07 (s, 3H). LC-ES/MS m/z (35C1/37C1) 265.2/267.1 (M+l). The compound is dissolved in MeOH (70 mL). The enantiomers are separated in 21 mg injections by supercritical fluid chromatography on two CHIRALPAK AD-H columns (2 x 25 cm, 5 muiotaeta) stringed in series. Mobile phase: 20% isopropanol/carbon dioxide. Flow rate: 65 mL/min. Detection: 215 nm. Each run is 6.48 min. The first eluting peak is obtained as Isomer 1 and the second eluting peak is obtained as the title compound, Isomer 2 (4.13 g, 100% enantiomeric excess). The enantiomeric excess is determined by SFC on a CHIRALPAK AD-H (4.6 x 100 mm, 5 muiotaeta) column using 20% isopropanol/carbon dioxide. Flow rate: 2.5 mL/min. Detection: 215 nm. Isomer 1 TR = 2.53 min. Isomer 2 (title compound) TR = 3.06 min.The compound of Example 1 can also be named or referred to as 2-chloro-4- [ [( 1 R,2R)-2-hydroxy-2-methyl-cyclopentyl] amino] -3 -methyl-benzonitrile.
  • 2
  • [ 796600-15-2 ]
  • [ 20412-66-2 ]
  • [ 1430230-83-3 ]
  • [ 1430230-84-4 ]
  • 3
  • [ 796600-15-2 ]
  • [ 20412-66-2 ]
  • 2-chloro-4-[[(±)-2-hydroxy-2-methylcyclopentyl]amino]-3-methylbenzonitrile [ No CAS ]
 

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