Water → 1-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(hydroxymethyl)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylate

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Reaction Steps

1-(2-(Trimethylsilyl)ethyl) 1′-tert-butyl 5-formylspiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (553 mg, 1.24 mmol) was dissolved in ethanol (12 mL). Thereafter, sodium borohydride (76.0 mg, 2.01 mmol) was added to the above obtained solution under cooling on ice, and the thus obtained mixture was then stirred at the same temperature as above for 30 minutes. Thereafter, water was added to the reaction solution, and the mixed solution was then extracted with chloroform. The organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-(hydroxymethyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (473 mg, 85%) in the form of a light yellow solid.

Provenance & Evidence