Boron tribromide → (+/-)-trans-6-Ethyl-8a-(3-hydroxyphenyl)-3-methyl-2-phenylaminocarbonyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline

HRID 2870Notes

Reaction equation

[CH2:1]([N:3]1[CH2:12][CH2:11][C@:10]2([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=3)[C@H:5]([CH2:6][C:7]3[C:23]([CH3:24])=[C:22]([C:25]([NH:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[O:26])[NH:21][C:8]=3[CH2:9]2)[CH2:4]1)[CH3:2].B(Br)(Br)Br>>[CH2:1]([N:3]1[CH2:12][CH2:11][C@:10]2([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=3)[C@H:5]([CH2:6][C:7]3[C:23]([CH3:24])=[C:22]([C:25]([NH:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[O:26])[NH:21][C:8]=3[CH2:9]2)[CH2:4]1)[CH3:2]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 22883679(+/-)-trans-6-Ethyl-3-methyl-8a-(3-methoxyphenyl)-2-phenylaminocarbonyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline

Product 1

HCID 22883680(+/-)-trans-6-Ethyl-8a-(3-hydroxyphenyl)-3-methyl-2-phenylaminocarbonyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinolineYield 22.1%

Procedure

0.28 g of (±)-trans-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-2-phenylaminocarbonyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline were treated with 0.35 (1.9 mmol) of boron tribromide as described in example 2. The residue was purified by flash chromatography (EtOAc/MeOH/conc. NH4OH 80:20:2) yielding 0.06 g of the title compound. M.p.=271°-272° C.

Workup

customThe residue was purified by flash chromatography (EtOAc/MeOH/conc. NH4OH 80:20:2)

Sources & evidence

ORD record: ord-d7d0772f09424c2a8285b114d4b7d007
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05731322

Reaction notes

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