HCID 66988034, compound → HCID 59668841, compound

Temperature

4 °C

A solution of 3-(methoxymethylcarbamoyl)azetidine-1-carboxylic acid tert-butyl ester (1.06 g, 4.34 mmol) in anhydrous tetrahydrofuran (15 mL) was cooled to 4° C. under argon gas. 2M solution of isopropyl magnesium chloride (4.35 mL, 8.68 mmol) was added dropwise and the resulting reaction mixture was stirred at 4° C. for 5 min. The temperature was allowed to rise to RT and stirred for 1 h then the mixture was stirred at 40° C. for 1 h. The reaction mixture was quenched by addition of a saturated solution of ammonium chloride (5 mL) and water (10 mL). The aqueous phase was extracted with ethyl acetate (3×20 mL). The organic layer was dried over sodium sulfate, filtered and the solvents reduced in vacuo to afford the title compound as a pale yellow oil (950 mg, 96%) 1H NMR (400 MHz, CDCl3): δ 4.03-4.01 (4 H, m), 3.59-3.59 (1 H, m), 2.61-2.61 (1 H, m), 1.43 (9 H, s), 1.11 (6 H, d, J=6.94 Hz).

1. customthe resulting reaction mixture
2. customto rise to RT
3. stirringstirred for 1 h
4. stirringthe mixture was stirred at 40° C. for 1 h
5. customThe reaction mixture was quenched by addition of a saturated solution of ammonium chloride (5 mL) and water (10 mL)
6. extractionThe aqueous phase was extracted with ethyl acetate (3×20 mL)
7. dry with materialThe organic layer was dried over sodium sulfate
8. filtrationfiltered

ORD record

ord-60b20e24a3634df6ad28a9d420ff8abd

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394796B2