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Chemical Structure| 474023-54-6 Chemical Structure| 474023-54-6

Structure of 474023-54-6

Chemical Structure| 474023-54-6

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Product Details of [ 474023-54-6 ]

CAS No. :474023-54-6
Formula : C12H21NO3
M.W : 227.30
SMILES Code : O=C(N1[C@@H](CC=C)C[C@@H](O)C1)OC(C)(C)C

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Application In Synthesis of [ 474023-54-6 ]

* 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 [ 474023-54-6 ]

[ 474023-54-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 109431-87-0 ]
  • [ 474023-54-6 ]
YieldReaction ConditionsOperation in experiment
70% Step A: f2S.4RVl-Boc-2-allyl-4-hydroxypyrroridine; [460] (3R)-l-BOC-3-hydroxypyrrolidine (1 g, 5.34 mmol) was dissolved in diethylether (50ml), and filled with nitrogen. The reaction mixture was cooled to -78C, N,N,N',N'-tetramethylethylenediamine (620 mg, 5.34 mmol) was added, and sec- butyllithium (1.4M cyclohexane solution 4.45 ml, 6.23 mmol) was slowly added. After being stirred for 30 min at the same temperature, dimethylsulfate (1.44 g, 10.68 mmol) was dissolved in diethylether (10 ml). The reaction solution was slowly heated to rt, diluted with water (12 ml), and extracted with diethylether. The organic extracts were dried over MgSO 4 , and the residue was purified by column chromatography (eluent,EtOAc/Hex = 1/4) to give the title compound (840 mg, 70 %).[461] MS[M+H] = 228(M+1)
  • 2
  • [ 109431-87-0 ]
  • [ 106-95-6 ]
  • [ 474023-54-6 ]
YieldReaction ConditionsOperation in experiment
56% A solution of N-Boc-3-Rhydroxypyrrolidine (3.0 g, 16.0 mmol), and TMEDA (6.4 mL, 40. 1 mmol) is dissolved in THF (50 mL) and cooled to-78 C. To this reaction mixture is added a solution of 1.3 M sec-butyl lithium (50 mL) in cyclohexanes with stirring. The resulting orange-colored mixture is allowed to warm to -40 C and stirred for 2.75 hours. The mixture is again cooled to-78 C and allyl bromide (3.1 mL, 35.3 mmol) is added. This mixture is slowly warmed to room temperature with stirring over 4.5 hours. The reaction is quenched with aq. NH4CI solution and extracted with ethyl acetate (150 mL). The organic layer is then dried over Na2SO4, filtered and concentrated in vacuo. The oily residue is purified over silica gel (CH2CI2/acetone, 3: 1) to afford the desired product (2.0 g, 56%) as a clear oil.
 

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