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Chemical Structure| 161521-10-4 Chemical Structure| 161521-10-4

Structure of 161521-10-4

Chemical Structure| 161521-10-4

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Product Details of [ 161521-10-4 ]

CAS No. :161521-10-4
Formula : C11H20N2O4
M.W : 244.29
SMILES Code : O=C(NC1(CC1)C(N(C)OC)=O)OC(C)(C)C

Safety of [ 161521-10-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H228-H315-H319
Precautionary Statements:P240-P210-P241-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313
Class:4.1
UN#:1325
Packing Group:

Application In Synthesis of [ 161521-10-4 ]

* 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.

  • Downstream synthetic route of [ 161521-10-4 ]

[ 161521-10-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 161521-10-4 ]
  • [ 107259-06-3 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride; In diethyl ether; at 20℃; for 0.666667h; To a 0.05 M solution of [l-(methoxy-methyl-carbamoyl)cyclopropyl]carbamic acid fert-butyl ester in Et2O (80 mL, 4.0 mmol) at room temperature was added dropwise lithium aluminum hydride (1.0 M in Et2O, 5 mL, 5.0 mmol). The reaction mixture was stirred for another 20 min and then quenched with 6 mL of a solution OfKHSO4 in water. The layers were separated and the aqueous layer was extracted with Et2O. The combined organic layers were washed with 1 N HCl, saturated NaHCO3, and brine, dried (Na2SO4), and concentrated to yield (l-formylcyclopropyl)carbamic acid tert-butyl ester as a colorless oil (393 mg) which was used immediately in the next step without further purification.
Step 1-D:To a solution of Id (1.39 g, 5.73 mmol) in methylene chloride (20 mL) is cooled to -78C and is added dropwise a IM solution of DiBAl-H in methylene chloride. The reaction is stirred at -78C for 3 hours and then quenched with IN solution of Rochelle salt (25 mL). The aqueous phase is then extracted with methylene chloride. The combined organic layers are dried over MgSO4, filtered and concentrated in vacuo. The residue is chromatographed on silica gel (gradient: EtOAc/hexane; 0: 1 to 1 :1) to afford Ie (0.57 g). Found m/z ES+ = 186.
Step 5; [0201] To a 0.05 M solution of [l-(methoxy-methyl-carbamoyl)cyclopropyl]carbamic acid tert-butyl ester in Et2O (80 mL, 4.0 mmol) at room temperature was added dropwise lithium aluminum hydride (1.0 M in Et2O, 5 mL, 5.0 mmol). The reaction mixture was stirred for another 20 min and then quenched with 6 mL of a solution of KHSO4 in water. The layers were separated and the aqueous layer was extracted with Et2O. The combined organic layers were washed with 1 N HCl, saturated NaHCO3, and brine, dried (Na2SO4), and concentrated EPO <DP n="72"/>to yield (l-formylcyclopropyl)carbamic acid tert-butyl ester as a colorless oil (393 mg) which was used immediately in the next step without further purification.
With lithium aluminium tetrahydride; In diethyl ether; at 0℃; for 2h;Inert atmosphere; Tert-butyl (1-(methoxy(methyl)carbamoyl)cyclopropyl) carbamate 13 (500 mg) was dissolved in anhydrous Et20 (50 ml_) under argon and cooled to 0C. Lithium Aluminum Hydride(3 mL, 1 M in Et20) was added dropwise and the reaction mixture was stirred for 2h at this temperature. The reaction was quenched by addition of 1 N HCI (2.5 mL) and stirred vigorously for a few minutes. The organic layer was extracted with 1 N HCI and brine, dried over Na2S04, filtered and concentrated to obtain the product aldehyde 14 as a colorless oil. Use crude in the next step.

 

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