Hydrochloric Acid → 3-Azido-3-methylbutan-1-ol

Borane dimethylsulfide complex (2 M, 15 mL, 30 mmol) was added over 20 min to 3-azido-3-methylbutanoic acid (4.25 g, 30 mmol) in THF (15 mL) at room temperature. The reaction was stirred for 16 h. The reaction mixture was cooled in an ice bath and methanol (50 mL) was added dropwise to the solution over 15 min. Then 4 M HCl in dioxanes (7.5 mL, 30 mmol) was added to the reaction mixture and stirred for 30 min. The reaction mixture was concentrated on a rotovap to a colorless liquid (3.33 g, 91%). This material was used without further purification. 1H NMR (CDCl3, 400 MHz): δ 1.35 (s, 6H), 1.74-1.78 (t, J=6.4, 2H), 3.75-3.80 (t, J=6.4, 2H). LRMS (ESI+) for C5H11N3O (129.1); Found: did not ionize.

1. temperatureThe reaction mixture was cooled in an ice bath
2. stirringstirred for 30 min
3. concentrationThe reaction mixture was concentrated on a rotovap to a colorless liquid (3.33 g, 91%)
4. customThis material was used without further purification

ORD record

ord-1633b11de2004c92a58d935ed638fa0c

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278482B2