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

HRID 2863Notes

Reaction equation

[ClH:1].[CH2:2]([O:6][C:7]([C:9]1[NH:31][C:12]2[CH2:13][C@@:14]3([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([O:29]C)[CH:24]=4)[C@H:19]([CH2:20][C:11]=2[C:10]=1[CH3:32])[CH2:18][N:17]([CH2:21][CH3:22])[CH2:16][CH2:15]3)=[O:8])[CH:3]([CH3:5])[CH3:4].B(Br)(Br)Br>>[ClH:1].[CH2:2]([O:6][C:7]([C:9]1[NH:31][C:12]2[CH2:13][C@@:14]3([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=4)[C@H:19]([CH2:20][C:11]=2[C:10]=1[CH3:32])[CH2:18][N:17]([CH2:21][CH3:22])[CH2:16][CH2:15]3)=[O:8])[CH:3]([CH3:5])[CH3:4]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 22883663(+/-)-trans-2-(i-butoxycarbonyl)-6-ethyl-3-methyl-8a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline hydrochloride

Product 1

HCID 22883665(+/-)-trans-2-(i-Butoxycarbonyl)-6-ethyl-8a-(3-hydroxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline hydrochloride

Procedure

0.56 g of (±)-trans-2-(i-butoxycarbonyl)-6-ethyl-3-methyl-8a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline hydrochloride were treated with 0.68 ml (7.26 mmol) of boron tribromide as described in example 2. The residue was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 75:25:2.5) and then crystallised from AcOEt yielding 0.1 g of the title compound. M.p.=196°-198° C.

Workup

customThe residue was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 75:25:2.5)
customcrystallised from AcOEt yielding 0.1 g of the title compound

Sources & evidence

ORD record: ord-c4dcc751dbde49eaa01591fb6c337bfc
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05731322

Reaction notes

Loading…