Reaktion #71308

Reaktionsgleichung

lithium aluminium hydride

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

lithium aluminium hydride

→

title compound

Ausbeute 74.4%

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

Ausbeute 74.4%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter 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
   Sonstigebefore being carefully quenched with H2O (10 mL) and 2N NaOH (10 mL)
4. 4
   FiltrationThe resulting mixture was filtered
5. 5
   Sonstigepartitioned between EtOAc and brine
6. 6
   SonstigeThe organic layer was separated
7. 7
   Sonstigedried on Na2SO4 and solvent
8. 8
   Sonstigeevaporated in vacuo
9. 9
   Sonstigeto give a dark yellow oil
10. 10
    SonstigePurification by flash chromatography (0-100% EtOAc in Hept.)

Vorschrift

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.

Quelle