반응 #71308

반응 방정식

lithium aluminium hydride

methyl 1-(1-methylethylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylate

lithium aluminium hydride

→

title compound

수율 74.4%

N-(5-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide

수율 74.4%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도After this time the reaction mixture was again cooled to 0° C.
2. 2
   workup.STIRRINGthe whole stirred at room temperature for 30 min
3. 3
   기타before being carefully quenched with H2O (10 mL) and 2N NaOH (10 mL)
4. 4
   여과The resulting mixture was filtered
5. 5
   기타partitioned between EtOAc and brine
6. 6
   기타The organic layer was separated
7. 7
   기타dried on Na2SO4 and solvent
8. 8
   기타evaporated in vacuo
9. 9
   기타to give a dark yellow oil
10. 10
    기타Purification by flash chromatography (0-100% EtOAc in Hept.)

실험 절차

At 0° C. lithium aluminium hydride (2.102 mL, 5.04 mmol) was added dropwise to a stirred solution of methyl 1-(1-methylethylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylate (1 g, 3.36 mmol) in tetrahydrofuran (dry) (25 mL). Mixture warmed to rt and stirred for 4 hr. After this time the reaction mixture was again cooled to 0° C. and more lithium aluminium hydride (2.102 mL, 5.04 mmol) added and the whole stirred at room temperature for 30 min before being carefully quenched with H2O (10 mL) and 2N NaOH (10 mL). The resulting mixture was filtered and partitioned between EtOAc and brine. The organic layer was separated, dried on Na2SO4 and solvent evaporated in vacuo to give a dark yellow oil. Purification by flash chromatography (0-100% EtOAc in Hept.) afforded the title compound as a colourless oil (670 mg 2.5 mmol, 74%). MS (ESI): m/z [M−H]− 268.0.

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