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

HRID 2868
Notes
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Reaction equation

HRID 2868 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[NH:32][C:14]2[CH2:15][C@@:16]3([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([O:30]C)[CH:25]=4)[C@H:21]([CH2:22][C:13]=2[C:12]=1[CH3:33])[CH2:20][N:19]([CH3:23])[CH2:18][CH2:17]3)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.[ClH:38].CCOCC>CO>[ClH:38].[CH2:1]([NH:8][C:9]([C:11]1[NH:32][C:14]2[CH2:15][C@@:16]3([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=4)[C@H:21]([CH2:22][C:13]=2[C:12]=1[CH3:33])[CH2:20][N:19]([CH3:23])[CH2:18][CH2:17]3)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 10953452Ether hydrochlorideHCID 22883641(+/-)-trans-2-Benzylaminocarbonyl-3,6-dimethyl-8a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline

Product 1

HCID 22883639(+/-)-trans-2-Benzylaminocarbonyl-3,6-dimethyl-8a-(3-hydroxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.38 g of (±)-trans-2-benzylaminocarbonyl-3,6-dimethyl-8a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline were treated with 0.55 ml (5.7 mmol) of boron tribromide as described in example 2. The residue was dissolved in MeOH and the solution brought to acidic pH with HCl/Et2O. The solvent was evaporated in vacuo and the solid crystallised from a mixture of acetone/MeOH=1:1, yielding 0.15 g of the title compound. M.p.=297°-299° C. C27H31N3 O2.HCl I.R. (KBr): 3290, 2910, 1650, 1540, 1320cm-1

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe solid crystallised from a mixture of acetone/MeOH=1:1

Sources & evidence

ORD record
ord-2895d0d365944737af7826beeea98209
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05731322

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes