tert-butyl (6S)-6-(hydroxymethyl)-5-azaspiro[2.4]heptane-5-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To (S)-tert-butyl 6-(hydroxymethyl)-5-azaspiro[2.4]heptane-5-carboxylate (Intermediate 59, 2.2 g, 9.7 mmol) dissolved in 10 ml of DCM, TEMPO (306 mg, 1.9 mmol) and BAIB (3.43 mg, 10.6 mmol) were added. After 2 hours at 25° C., the reaction is diluted with DCM (150 ml), washed with an aqueous solution of Na2S2O3 then with water, dried (Na2SO4) and evaporated to obtain a crude that was purified by silica gel chromatography (petroleum ether to petroleum ether/ethylacetate 95/5). (S)-tert-butyl 6-formyl-5-azaspiro[2.4]heptane-5-carboxylate was obtained as light yellow solid (1.8 g). washed with an aqueous solution of Na2S2O3 with water, dried (Na2SO4) evaporated to obtain a crude that was purified by silica gel chromatography (petroleum ether to petroleum ether/ethylacetate 95/5)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To (S)-tert-butyl 6-(hydroxymethyl)-5-azaspiro[2.4]heptane-5-carboxylate (Intermediate 59, 2.2 g, 9.7 mmol) dissolved in 10 ml of DCM, TEMPO (306 mg, 1.9 mmol) and BAIB (3.43 mg, 10.6 mmol) were added. After 2 hours at 25° C., the reaction is diluted with DCM (150 ml), washed with an aqueous solution of Na2S2O3 then with water, dried (Na2SO4) and evaporated to obtain a crude that was purified by silica gel chromatography (petroleum ether to petroleum ether/ethylacetate 95/5). (S)-tert-butyl 6-formyl-5-azaspiro[2.4]heptane-5-carboxylate was obtained as light yellow solid (1.8 g). washed with an aqueous solution of Na2S2O3 with water, dried (Na2SO4) evaporated to obtain a crude that was purified by silica gel chromatography (petroleum ether to petroleum ether/ethylacetate 95/5)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To (S)-tert-butyl 6-(hydroxymethyl)-5-azaspiro[2.4]heptane-5-carboxylate (Intermediate 59, 2.2 g, 9.7 mmol) dissolved in 10 ml of DCM, TEMPO (306 mg, 1.9 mmol) and BAIB (3.43 mg, 10.6 mmol) were added. After 2 hours at 25° C., the reaction is diluted with DCM (150 ml), washed with an aqueous solution of Na2S2O3 then with water, dried (Na2SO4) and evaporated to obtain a crude that was purified by silica gel chromatography (petroleum ether to petroleum ether/ethylacetate 95/5). (S)-tert-butyl 6-formyl-5-azaspiro[2.4]heptane-5-carboxylate was obtained as light yellow solid (1.8 g). washed with an aqueous solution of Na2S2O3 with water, dried (Na2SO4) evaporated to obtain a crude that was purified by silica gel chromatography (petroleum ether to petroleum ether/ethylacetate 95/5)