Water → HCID 67775164, compound

To LAH (1 M solution in THF) (69.8 mL, 69.84 mmol) was added a solution of tert-butyl (2S,3S)-1-(3-hydroxyazetidin-1-yl)-3-methyl-1-oxopentan-2-ylcarbamate (Compound F2.1) (5 g, 17.5 mmol) in anhydrous THF (24 mL) dropwise (1 h) under nitrogen. The reaction mixture was stirred at rt for 1 h and then heated at 60° C. over night. The reaction mixture was cooled to 0° C. Water (3.5 ml) was added dropwise, followed by 15% aq. NaOH (3.5 ml), THF (50 ml) and water (7.5 ml). The mixture was allowed to reach rt and stirred for 30 min. The solids were filtered off and washed with THF. The filtrate was dried over Na2SO4 and concentrated under reduced pressure to give the title compound as colorless oil (2.8 g, 86%). The product was used in the next step without further purification. 1H NMR (600 MHz, CDCl3) δ 0.80 (d, 3H), 0.91 (t, 3H), 1.10-1.23 (m, 1H), 1.25-1.38 (m, 1H), 1.53-1.63 (m, 1H), 2.15-2.30 (m, 3H), 2.36 (s, 3H), 2.38-2.47 (m, 2H), 2.77-2.84 (m, 1H), 2.89-2.97 (m, 1H), 3.50-3.64 (m, 2H), 4.33-4.44 (m, 1H).

1. temperatureheated at 60° C. over night
2. temperatureThe reaction mixture was cooled to 0° C
3. customto reach rt
4. stirringstirred for 30 min
5. filtrationThe solids were filtered off
6. washwashed with THF
7. dry with materialThe filtrate was dried over Na2SO4
8. concentrationconcentrated under reduced pressure

ORD record

ord-ea96b2bbb9774a31bd238beb1f908b30

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08361998B2