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

HRID 2876

Reaction equation

HRID 2876 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]([C:5]1[NH:27][C:8]2[CH2:9][C@@:10]3([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([O:25]C)[CH:20]=4)[C@H:15]([CH2:16][C:7]=2[C:6]=1[CH3:28])[CH2:14][N:13]([CH2:17][CH3:18])[CH2:12][CH2:11]3)=[O:4].B(Br)(Br)Br.[ClH:34].CCOCC>CO>[ClH:34].[CH3:29][N:2]([CH3:1])[C:3]([C:5]1[NH:27][C:8]2[CH2:9][C@@:10]3([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=4)[C@H:15]([CH2:16][C:7]=2[C:6]=1[CH3:28])[CH2:14][N:13]([CH2:17][CH3:18])[CH2:12][CH2:11]3)=[O:4]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 10953452Ether hydrochlorideHCID 22883662(+/-)trans-2-dimethylaminocarbonyl-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g] isoquinoline

Product 1

HCID 22883660(+/-)-trans-2-Dimethylaminocarbonyl-6-ethyl-8a-(3-hydroxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.5 g (1.25 mmol) of (±)trans-2-dimethylaminocarbonyl-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g] isoquinoline were treated with 0.725 ml (7.5 mmol) of boron tribromide as described in example 2. The etude product was dissolved in MeOH and the solution brought to acidic pH with HCl/Et2O. The solvent was evaporated in vacuo and the solid crystallized from EtOH, yielding 0.15 g of the title compound. M.p.=305° C. dec.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe solid crystallized from EtOH

Sources & evidence

ORD record
ord-3ae2e96f1f8c4014ac444d242c55c3da
Source dataset
uspto-grants-1998_03
Patent number
US05731322

Linked notes

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