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Chemical Structure| 272438-11-6 Chemical Structure| 272438-11-6

Structure of 272438-11-6

Chemical Structure| 272438-11-6

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Product Details of [ 272438-11-6 ]

CAS No. :272438-11-6
Formula : C15H17NO4
M.W : 275.30
SMILES Code : COC(=O)C1=CC2=C(C=C1)N(C=C2)C(=O)OC(C)(C)C
MDL No. :MFCD13183437

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Application In Synthesis of [ 272438-11-6 ]

* 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 [ 272438-11-6 ]

[ 272438-11-6 ] Synthesis Path-Downstream   1~2

  • 1
  • ammonium chloride [ No CAS ]
  • [ 272438-11-6 ]
  • [ 279255-90-2 ]
YieldReaction ConditionsOperation in experiment
With diisobutylaluminium hydride; In tetrahydrofuran; methanol; water; toluene; Step 2 To a solution of N-tert-butoxycarbonylindole-5-carboxylic acid methyl ester (23.6 g, 85.7 mmol) in dry tetrahydrofuran (225 mL) at -78 C. was added 1.5 M DIBALH in toluene (171 mL, 257 mmol). After 2 h, the reaction mixture was quenched by the slow addition of methanol (45 mL), water (60 mL), and saturated aqueous NH4Cl (30 mL). The cold bath was removed and after stirring for an additional 1 h, the reaction mixture was filtered over Celite. The Celite cake was washed with tetrahydrofuran and the filtrate was concentrated to remove the more volatile tetrahydrofuran. The biphasic mixture was extracted with ethyl acetate. The combined organic layers were washed with water and the aqueous layer back extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated to afford N-tert-butoxycarbonylindol-5-yl methanol (21.2 g).
  • 2
  • [ 272438-11-6 ]
  • [ 279255-90-2 ]
YieldReaction ConditionsOperation in experiment
With ammonium chloride; diisobutylaluminium hydride; In tetrahydrofuran; methanol; water; ethyl acetate; toluene; Step 3 To a cooled solution (-78 C.) of methyl (N-tert-butoxycarbonyl)indole-5-carboxylate (7.6 g, 27.9 mmol) in dry tetrahydrofuran (75 mL) was added diisobutylaluminum hydride (57 mL, 1.5 M in toluene) via syringe over 5 min. After 1.5 h, the reaction mixture was quenched by careful addition of methanol (15 mL) and allowed to warm to room temperature over 45 min. Water (20 mL) and a saturated solution of ammonium chloride(10 mL) was added with vigorous stirring and the resultant inorganic precipitate was removed by filtration. The filtrate was condensed on the roto-evaporator and the residue was partitioned between a 1:1 mixture of ethyl acetate/water (160 mL). The ethyl acetate phase was washed with brine and the aqueous phases back extracted with ethyl acetate. The organic phase was combined, dried with magnesium sulfate, filtered and concentrated to provide (N-tert-butoxycarbonyl)indole-5-methanol (7.35 g) as a semi-viscous yellow oil which was used in the next step without further purification.
 

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