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

HRID 2872

Reaction equation

HRID 2872 reaction equation
[CH:1]([N:4]([CH:31]([CH3:33])[CH3:32])[C:5]([C:7]1[NH:29][C:10]2[CH2:11][C@@:12]3([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27]C)[CH:22]=4)[C@H:17]([CH2:18][C:9]=2[C:8]=1[CH3:30])[CH2:16][N:15]([CH2:19][CH3:20])[CH2:14][CH2:13]3)=[O:6])([CH3:3])[CH3:2].B(Br)(Br)Br.[ClH:38].CCOCC>CO>[ClH:38].[CH:31]([N:4]([CH:1]([CH3:2])[CH3:3])[C:5]([C:7]1[NH:29][C:10]2[CH2:11][C@@:12]3([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=4)[C@H:17]([CH2:18][C:9]=2[C:8]=1[CH3:30])[CH2:16][N:15]([CH2:19][CH3:20])[CH2:14][CH2:13]3)=[O:6])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 10953452Ether hydrochlorideHCID 22883659(+/-)-trans-2-diisopropylaminocarbonyl-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 22883657(+/-)-trans-2-Diisopropylaminocarbonyl-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

1.0 g (2.2 mmol) of (±)-trans-2-diisopropylaminocarbonyl-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 1.15 ml (12.0 mmol) of boron tribromide as described in example 2. The crude 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 acetone, yielding 0.5 g of the title compound. M.p.=263°-265° C.

Workup

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

Sources & evidence

ORD record
ord-85e68abf33ca4928bc83045893ab7a1b
Source dataset
uspto-grants-1998_03
Patent number
US05731322

Linked notes

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