Benzylamine → cis-6-Benzylamino-8-methyl-1,2,4,4a,9,9a-hexahydro-3-aza-fluorene-3-carboxylic acid ethyl ester

Temperatur

80 °C

cis-6-Bromo-8-methyl-1,2,4,4a,9,9a-hexahydro-3-aza-fluorene-3-carboxylic acid ethyl ester (68 mg, 0.2 mmol), benzylamine (64 mg, 0.6 mmol), NaOt-Bu (58 mg, 0.3 mmol) and (2-biphenyl)di-t-butylphosphine (11 mg, 0.018 mmol) were dissolved in toluene (5.0 mL), and the solution was degassed. To the solution was added tris(dibenzylideneacetone)dipalladium (11 mg, 0.006 mmol), and the reaction mixture was heated at 80° C. for 15 h under Ar. The reaction mixture was cooled to 20° C. and diluted with CH2Cl2. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was filtered through short silica gel column (Hex/EtOAc 7/3) to obtain crude cis-6-benzylamino-8-methyl-1,2,4,4a,9,9a-hexahydro-3-aza-fluorene-3-carboxylic acid ethyl ester (66 mg, 0.18 mmol)

1. customthe solution was degassed
2. temperatureThe reaction mixture was cooled to 20° C.
3. washThe organic layer was washed with brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. filtrationThe residue was filtered through short silica gel column (Hex/EtOAc 7/3)

ORD-Eintrag

ord-8086119f58564dfa9dcb73d2a4021db7

Quelldatensatz

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07795436B2