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

Temperature

-78 °C

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).

1. customResulting
2. customreaction mixture
3. customAfter complete consumption of starting material, reaction mixture
4. customwas quenched by methanol (0.2 mL)
5. additionfollowed by addition of saturated solution of sodium potassium tartarate salt (0.5 mL) at −78° C.
6. extractionextracted with DCM (3×25 mL)
7. dry with materialCombined organic layer was dried over sodium sulphate
8. concentrationconcentrated under reduced pressure

ORD record

ord-a6e67926a0b647a38d885473e26e0aab

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09131697B2