Boron tribromide → HCID 22883681, compound

HRID 2878Notes

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]([N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]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]([N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)=[O:26])[NH:21][C:8]=3[CH2:9]2)[CH2:4]1)[CH3:2]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 22883683HCID 22883683, compound

Product 1

HCID 22883681HCID 22883681, compoundYield 23.3%

Procedure

0.63 g (1.37 mmol) of (±)-trans-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-2-pyrrolidinocarbonyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline were treated with 0.77 ml (8.22 mmol) of boron tribromide as described in example 2. The residue was purified by flash chromatography (EtOAc/MeOH/conc. NH4OH 80:20:0.5). The resulting solid was triturated with Et2O, yielding 0.13 g of the title compound. M.p.=224°-226° C.

Workup

customThe residue was purified by flash chromatography (EtOAc/MeOH/conc. NH4OH 80:20:0.5)
customThe resulting solid was triturated with Et2O

Sources & evidence

ORD record: ord-e576ebaa84304ffda5a1fb2e2ebe1efc
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05731322

Reaction notes

Loading…