2,2,2-Trifluoroethylamine hydrochloride → 3-azido-3-methyl-N-(2,2,2-trifluoroethyl)butanamide

To a stirred ice cold solution of 2,2,2-trifluoroethanamine hydrochloride (7.10 g, 1 equiv, 52.4 mmol) and DIEA (18.0 mL, 2.0 equiv, 0.103 mol) in anhydrous DCE (150 mL) was added 3-azido-3-methylbutanoyl chloride (8.46 g, 52.4 mmol) in small portions. The ice bath was removed and the reaction was stirred and left at room temperature for 3 h. Water (150 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 (2×150 mL) and brine (150 mL). It was dried over anhydrous MgSO4, filtered, concentrated and dried under high vacuum to give a crude oil (10.9 g, 94.4). This material was used without further purification. 1H NMR (CDCl3, 400 MHz): δ 1.42 (s, 6H), 2.40 (s, 2H), (dq, J=2.4 & 8.8, 2H). LRMS (ESI+) for C7H11F3N4O (224.1); Found: 225 (MH+).

1. customThe ice bath was removed
2. additionWater (150 mL) was added to the reaction mixture
3. additionthe contents poured into a separatory funnel
4. customThe organic layer was separated
5. washwashed with 1 M HCl (2×150 mL) and brine (150 mL)
6. dry with materialIt was dried over anhydrous MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customdried under high vacuum
10. customto give a crude oil (10.9 g, 94.4)
11. customThis material was used without further purification

ORD record

ord-c181259ff82d460293278ed085719e36

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278482B2