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

HRID 1714147Notes

Reaction equation

C(O[C:4]([N:6]1[CH2:18][C@H:17]2[C@H:9]([CH2:10][C:11]3[C:16]2=[CH:15][C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][C:12]=3[CH3:25])[CH2:8][CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:4][N:6]1[CH2:18][C@H:17]2[C@H:9]([CH2:10][C:11]3[C:16]2=[CH:15][C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][C:12]=3[CH3:25])[CH2:8][CH2:7]1

Participants

Conditions

Temperature: 20 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-296f14bedfff4f5db63800eeddc516a8
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795436B2

Reaction notes

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