Triethylsilane → cis-3-Benzyl-6-bromo-8-methyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluorene

HRID 1714142Notes

Reaction equation

[CH2:1]([N:8]1[CH2:20][C@H:19]2[C@H:11]([C:12](=O)[C:13]3[C:18]2=[CH:17][C:16]([Br:21])=[CH:15][C:14]=3[CH3:22])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SiH](CC)(CC)CC>FC(F)(F)C(O)=O>[CH2:1]([N:8]1[CH2:20][C@H:19]2[C@H:11]([CH2:12][C:13]3[C:18]2=[CH:17][C:16]([Br:21])=[CH:15][C:14]=3[CH3:22])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of cis-3-Benzyl-6-bromo-8-methyl-1,2,3,4,4a,9a-hexahydro-3-aza-fluoren-9-one (1.5 g, 4.0 mmol) in trifluoroacetic acid (15 mL) was added Et3SiH (10 mL). The reaction mixture was stirred at 20° C. for 3 days then concentrated in vacuo. The residue was basified with NH4OH then extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed in silica gel column (Hex/EtOAc 9/1) to give the title compound (440 mg, 1.23 mmol): MS (ES) 356.1 (M+H).

Workup

concentrationthen concentrated in vacuo
extractionthen extracted with EtOAc
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was chromatographed in silica gel column (Hex/EtOAc 9/1)

Sources & evidence

ORD record: ord-4b70eaf9b33948d79c89b24e25d309a1
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795436B2

Reaction notes

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