Aluminium lithium hydride → HCID 59641697, compound

Compound 10 (263 mg, 1.07 mmol) was dissolved in tetrahydrofuran (12 mL) under a nitrogen atmosphere. Lithium aluminum hydride (3.7 mL of a 1 M solution in THF) was added dropwise over 20 min. The reaction was refluxed for 8 h, and then cooled to room temperature. It was quenched by successively adding water (1 mL, dropwise), 20% sodium hydroxide solution (1 mL), and then 25% ammonium hydroxide solution (2 mL). The resulting mixture was stirred for 30 min and then filtered through diatomaceous earth. The filtrate was dried over sodium sulfate and concentrated under vacuum to give the amine 11 (183 mg, 74% yield) as a red oil which was carried on without further purification: 1H NMR (500 MHz, CDCl3) δ 1.21-1.68 (m, 12H), 1.88-1.95 (m, 3H), 2.20-2.33 (m, 4H), 2.49-2.53 (m, 1H), 2.66-2.70 (m, 1H), 2.78-2.82 (m, 1H), 2.96-3.02 (m, 1H), 3.48-3.94 (m, 3H). m/z (ESI): 231 [C12H26N2O2+H]+.

1. temperatureThe reaction was refluxed for 8 h
2. customIt was quenched by successively adding water (1 mL
3. filtrationfiltered through diatomaceous earth
4. dry with materialThe filtrate was dried over sodium sulfate
5. concentrationconcentrated under vacuum

ORD record

ord-27d7d5fba6384ce4a47f12a7219a4163

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07317013B2