Aluminium lithium hydride → cis-3,8-Dimethyl-6-phenyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluorene

To a solution of cis-8-methyl-6-phenyl-1,2,4,4a,9,9a-hexahydro-3-aza-fluorene-3-carboxylic acid ethyl ester (20 mg, 0.060 mmol) in THF (1.0 mL) was added LiAlH4 (4.5 mg, 0.12 mmol) under Ar. The reaction mixture was stirred at 20° C. for 2 h then refluxed for 4 h. The reaction was cooled to 20° C. and quenched by addition of H2O and 1M NaOH. The quenched reaction mixture was extracted with CH2Cl2. The combined organic solution was dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed in silica gel column (Hex/EtOAc 1/1) to obtain the title compound (10 mg, 0.036 mmol): MS (ES) 278.2 (M+H).

1. temperaturethen refluxed for 4 h
2. temperatureThe reaction was cooled to 20° C.
3. customquenched by addition of H2O and 1M NaOH
4. customThe quenched reaction mixture
5. extractionwas extracted with CH2Cl2
6. dry with materialThe combined organic solution was dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue was chromatographed in silica gel column (Hex/EtOAc 1/1)

ORD record

ord-296f14bedfff4f5db63800eeddc516a8

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07795436B2