Azobisisobutyronitrile → Adamantane

A solution of 1-bromoadamantane (108 mg, 0.5 mmol, 1.0 equiv), the phosphonium supported chlorostanne (15) (82 mg, 0.1 mmol, 0.2 equiv), NaBH4 (28 mg, 0.75 mmol, 1.5 equiv) in CH3CN (2.5 mL, 0.2 M) was heated to reflux under Ar for 10 min. Then AIBN (8 mg, 0.05 mmol, 0.1 equiv) was added and the solution was heated to reflux for an additional 2 h. CHCl3 (5 mL) was added and the solution was filtered through Celite and the filtrate was concentrated under reduced pressure. The crude product was diluted with CHCl3(1 ml) and the tin residues were precipitated by adding Et2O (10 mL). The mixture was filtered through Celite and the filtrate was evaporated to afford pure adamantane in quantitative yield. No traces (<1%) of stannane impurities could be detected by NMR.

1. temperatureto reflux under Ar for 10 min
2. temperaturethe solution was heated
3. temperatureto reflux for an additional 2 h
4. filtrationthe solution was filtered through Celite
5. concentrationthe filtrate was concentrated under reduced pressure
6. additionThe crude product was diluted with CHCl3(1 ml)
7. customthe tin residues were precipitated
8. additionby adding Et2O (10 mL)
9. filtrationThe mixture was filtered through Celite
10. customthe filtrate was evaporated

ORD record

ord-931f068fda484f3481fa8dd02ccf553d

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08067440B2