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

HRID 1714142
Notes
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Reaction equation

HRID 1714142 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 16117545cis-3-Benzyl-6-bromo-8-methyl-1,2,3,4,4a,9a-hexahydro-3-aza-fluoren-9-one

Product 1

HCID 16117547cis-3-Benzyl-6-bromo-8-methyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluoreneYield 30.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

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

  1. concentrationthen concentrated in vacuo
  2. extractionthen extracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes