Hydrochloric Acid → HCID 60134493, compound

To a stirred ice cold solution of 4,4-dimethylpiperidine (4.21 g, 1 equiv, 37.2 mmol) and DIEA (9.73 mL, 1.5 equiv, 55.9 mmol) in anhydrous DCE (65 mL) was added 3-azido-3-methylbutanoyl chloride (6.02 g, 37.2 mmol) in small portions. The reaction was stirred and left at 0° C. for 1 h. Aqueous 1 M HCl (100 mL) was added to the reaction mixture and the contents poured into a separatory funnel. The organic layer was separated and washed with 1 M HCl (100 mL). It was dried over anhydrous MgSO4, filtered, concentrated and dried under high vacuum to give a crude oil (7.72 g, 87.1%). The crude oil was purified on an ISCO purification system with gradient elution from 20-50% ethyl acetate in hexanes. The desired fractions were collected and concentrated to give a colorless oil (6.00 g, yield: 67.7%). 1H NMR (CDCl3, 400 MHz): δ 0.98 (s, 6H), 1.32-1.39 (m, 4H), 1.45 (s, 6H), 2.52 (s, 2H), 3.42-3.47 (m, 2H), 3.55-3.60 (m, 2H). LRMS (ESI+) for C12H22N4O (238.2); Found: 239 (M+).

1. additionthe contents poured into a separatory funnel
2. customThe organic layer was separated
3. washwashed with 1 M HCl (100 mL)
4. dry with materialIt was dried over anhydrous MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customdried under high vacuum
8. customto give a crude oil (7.72 g, 87.1%)
9. customThe crude oil was purified on an ISCO purification system with gradient elution from 20-50% ethyl acetate in hexanes
10. customThe desired fractions were collected
11. concentrationconcentrated

ORD record

ord-636a46668da540f18ed3d115ba725162

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278482B2