Methyl iodide → HCID 66618095, compound

To a solution of tert-butyl(1S)-2,3-dihydro-1H-inden-1-ylcarbamate (1.82 g, 7.80 mmol) in THF (50.0 mL) under an atmosphere of argon at 0° C. was added 60% sodium hydride in mineral oil (968 mg, 24.2 mmol) and the suspension was allowed to warm to rt and stir for 30 min. Iodomethane (1.52 mL, 24.2 mmol) was added and the mixture was stirred overnight. The reaction was then quenched via addition of saturated ammonium chloride solution (10.0 mL) and was concentrated in vacuo. The mixture was then partitioned between water (20 mL) and DCM (50 mL) and the aqueous layer was extracted with DCM (3×50 mL). The combined organic layers were dried over MgSO4, filtered, concentrated in vacuo and purified by silica gel chromatography eluting with a gradient of 0 to 20% EtOAc in hexanes to afford the title compound as a clear, colorless oil (1.84 g, 95%). LC/MS: Rt=2.21 min, ES+ 248 (AA standard).

1. stirringthe mixture was stirred overnight
2. customThe reaction was then quenched via addition of saturated ammonium chloride solution (10.0 mL)
3. concentrationwas concentrated in vacuo
4. customThe mixture was then partitioned between water (20 mL) and DCM (50 mL)
5. extractionthe aqueous layer was extracted with DCM (3×50 mL)
6. dry with materialThe combined organic layers were dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. custompurified by silica gel chromatography
10. washeluting with a gradient of 0 to 20% EtOAc in hexanes

ORD record

ord-b1b80948cbae4dc7891b01581cc6a5e7

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08207177B2