Toluene → tert-butyl 6'-formyl-1'H-spiro[azetidine-3,3'-furo[3,4-c]pyridine]-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To the stirred solution of 1-tert-butyl 6′-ethyl 1′H-spiro[azetidine-3,3′-furo[3,4-c]pyridine]-1,6′-dicarboxylate (0.2 g, 0.60 mmol, 1 eq) in DCM (10 mL) at −78° C. under nitrogen atmosphere was added 25% DIBAL in toluene (0.255 g, 2.56 mL, 1.80 mmol, 3 eq). Resulting reaction mixture was stirred at −78° C. for 1 hour under nitrogen atmosphere. After complete consumption of starting material, reaction mixture was quenched by methanol (0.2 mL) followed by addition of saturated solution of sodium potassium tartarate salt (0.5 mL) at −78° C. and extracted with DCM (3×25 mL). Combined organic layer was dried over sodium sulphate, concentrated under reduced pressure to afford the title compound as brown solid (0.15 g, crude). Crude compound was used as such for the next reaction. 1H NMR (400 MHz, CDCl3) δ: 1.47 (s, 9H), 4.19 (d, J=10 Hz, 2H), 4.37 (d, J=10.04 Hz, 2H), 5.16 (s, 2H), 7.85 (s, 1H), 8.89 (s, 1H), 10.12 (s, 1H). LC-MS (m/z): 291.0 (M+H).

Provenance & Evidence