1,8-Diazabicyclo(5.4.0)undec-7-ene → (R)-1,2-Dihydroacenaphthylen-1-amine

Temperature

0 °C

To a cooled (0° C.) and stirred solution of (S)-acenaphthenol (1.74 g, 10.2 mmol) and diphenyl-phosphorylazide in toluene (17.5 ml) was added DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) (1.86 ml, 12.3 mmol) and stirring was continued at RT over a period of 20 h. The reaction mixture was extracted with toluene (2×50 ml), the combined organic phases washed with water, dried (MgSO4) and evaporated in vacuo. The crude product was dissolved in EtOH (120 ml) and hydrogenated at RT over PtO2 (0.24 g). The catalyst was filtered off, the solution evaporated in vacuo and the residue purified by column chromatography on silica gel (dichloromethane/MeOH 9:1) to yield (R)-acenaphthen-1-yl-amine (1.56 g) as a pink oil. MS: m/e=169 (M+).

1. extractionThe reaction mixture was extracted with toluene (2×50 ml)
2. washthe combined organic phases washed with water
3. dry with materialdried (MgSO4)
4. customevaporated in vacuo
5. dissolutionThe crude product was dissolved in EtOH (120 ml) and hydrogenated at RT over PtO2 (0.24 g)
6. filtrationThe catalyst was filtered off
7. customthe solution evaporated in vacuo
8. customthe residue purified by column chromatography on silica gel (dichloromethane/MeOH 9:1)

ORD record

ord-c1dfe4696d9440159c2fcae44185d98a

Source dataset

uspto-grants-2000_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06071925