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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1714142Generated: October 31, 2026

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

https://huagongshe.com/reaction/1714142

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylsilaneHCID 12052—
Reactantcis-3-Benzyl-6-bromo-8-methyl-1,2,3,4,4a,9a-hexahydro-3-aza-fluoren-9-oneHCID 16117545—
SolventTrifluoroacetic acidHCID 6422—
Productcis-3-Benzyl-6-bromo-8-methyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluoreneHCID 1611754730.8%

Reaction Conditions

Temperature20 °C

Reaction Steps

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).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07795436B2
Source datasetuspto-grants-2010_09
ORD IDord-4b70eaf9b33948d79c89b24e25d309a1
Source noteuspto-grants-2010_09