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

HRID 1714143Notes

Reaction equation

C([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)=[CH:15][C:14]=3[CH3:22])[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH3:22][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[CH2:12][C@H:11]1[C@@H:19]2[CH2:20][NH:8][CH2:9][CH2:10]1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of cis-3-benzyl-6-bromo-8-methyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluorene (50 mg, 0.14 mmol) in MeOH (2.0 mL) was added Pd(OH)2 (−10 mg, 20 wt %). The reaction mixture was stirred at 20° C. for 15 h under H2 atmosphere, filtered through celite and concentrated in vacuo. The residue was chromatographed in silica gel column (Hex/EtOAc 1/1) to give the title compound (21 mg, 1.1 mmol): MS (ES) 188.1 (M+H).

Workup

filtrationfiltered through celite and
concentrationconcentrated in vacuo
customThe residue was chromatographed in silica gel column (Hex/EtOAc 1/1)

Sources & evidence

ORD record: ord-fc5b5a07667a49a09ddb8bad3f83f5ff
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795436B2

Reaction notes

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