Aluminium lithium hydride → [2-(2-Aminomethyl-benzo[1,3]dioxol-5-yl)-1-methyl-ethyl]-ethyl-carbamic acid tert-butyl ester

Temperature

-60 °C

A flask containing 20 mL of freshly distilled THF was cooled to −60° C., and 615 mg (16.2 mmol) of lithium aluminum hydride (LAH) was added To the reaction mixture, a solution of 1.8 g (5.13 mmol) 2E in 20 mL of freshly distilled THF was added dropwise under argon atmosphere. The reaction mixture was allowed to stir at −60° C. for 20 minutes, 45 minutes at 0° C. and 2 hours at room temperature. The reaction was quenched with 430 μL of 15% NaOH and 3 mL of water and allowed to stir at room temperature for 10 minutes. The resulting solution was filtered through CELITE and the residue was washed with 100 mL of THF. The filtrate was concentrated to dryness under reduced pressure and purified by silica gel column chromatography using ethyl acetate as eluent to give 1.3 g (3.86 mmol, 75%) of 2F as a colorless gum (M+Na, 359).

1. customThe reaction was quenched with 430 μL of 15% NaOH and 3 mL of water
2. stirringto stir at room temperature for 10 minutes
3. filtrationThe resulting solution was filtered through CELITE
4. washthe residue was washed with 100 mL of THF
5. concentrationThe filtrate was concentrated to dryness under reduced pressure
6. custompurified by silica gel column chromatography

ORD record

ord-c7f4d2eb60fd47fdbbfed72994f65f2b

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07060847B2