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

HRID 2862Notes

Reaction equation

Cl.[CH2:2]([N:5]([CH2:32][CH2:33][CH3:34])[C:6]([N:8]1[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]([CH3:31])=[CH:9]1)[CH2:18][N:17]([CH2:21][CH3:22])[CH2:16][CH2:15]3)=[O:7])[CH2:3][CH3:4].B(Br)(Br)Br>>[CH2:2]([N:5]([CH2:32][CH2:33][CH3:34])[C:6]([N:8]1[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]([CH3:31])=[CH:9]1)[CH2:18][N:17]([CH2:21][CH3:22])[CH2:16][CH2:15]3)=[O:7])[CH2:3][CH3:4]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 86752326HCID 86752326, compound

Product 1

HCID 57276745(+/-)-trans-Dipropylaminocarbonyl-6-ethyl-8a-(3-hydroxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline

Procedure

0.56 g (1.15 mmol) of (±)-trans-dipropylaminocarbonyl-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 0.65 ml (7 mmol) of boron tribromide as described in example 2. The residue was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 75:25:2.5). The crude product was crystallised from acetone yielding 0.075 g of the title compound. M.p.=151°-153° C.

Workup

customThe residue was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 75:25:2.5)
customThe crude product was crystallised from acetone yielding 0.075 g of the title compound

Sources & evidence

ORD record: ord-9a47955b82844c658fba77886c3a3881
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05731322

Reaction notes

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