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

Reaktionsgleichung

Reaktionsgleichung von HRID 2868
[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

Komponenten

5

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-2895d0d365944737af7826beeea98209
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731322

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