tert-butyl (3aR,4S,9bR)-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline-1-carboxylate → tert-Butyl 4-phenyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline-1-carboxylate

HRID 550289Notes

Reaction equation

[C:1]1([C@@H:7]2[C@H:16]3[CH2:17][CH2:18][N:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@H:15]3[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[C:1]1([C:7]2[C:16]3[CH2:17][CH2:18][N:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:15]=3[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of tert-butyl (3aR*,4S*,9bR*)-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline-1-carboxylate (20.5 g, 58.6 mmol), manganese dioxide (50.9 g, 586 mmol) and toluene (400 ml) was stirred at 120° C. for 4 hrs. The reaction mixture was cooled to room temperature, insoluble materials were filtered off through celite, and the residue was washed with ethyl acetate. The filtrate and washings were combined and concentrated under reduced pressure. The obtained residue was subjected to column chromatography using basic silica gel, and eluted with hexane-ethyl acetate (10:1-8:1, v/v). The concentrated object fraction was recrystallized from hexane-ethyl acetate to give the title compound (11.7 g, 58%) as colorless needle crystals.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationinsoluble materials were filtered off through celite
washthe residue was washed with ethyl acetate
concentrationconcentrated under reduced pressure
washeluted with hexane-ethyl acetate (10:1-8:1
customThe concentrated object fraction was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record: ord-4116ce73c5fb4713bc10796c51a36d11
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943770B2

Reaction notes

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