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

HRID 2866Notes

Reaction equation

HRID 2866 reaction equation
[CH2:1]([N:3]([CH2:29][CH3:30])[C:4]([C:6]1[NH:18][C:17]2[CH2:16][C@@H:15]3[C@:10]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([O:26]C)[CH:21]=4)([CH2:11][CH2:12][N:13]([CH3:19])[CH2:14]3)[CH2:9][C:8]=2[C:7]=1[CH3:28])=[O:5])[CH3:2].B(Br)(Br)Br>>[CH2:29]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[NH:18][C:17]2[CH2:16][C@@H:15]3[C@:10]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=4)([CH2:11][CH2:12][N:13]([CH3:19])[CH2:14]3)[CH2:9][C:8]=2[C:7]=1[CH3:28])=[O:5])[CH3:30]

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 70106403(+/-)-trans-2-diethylaminocarbonyl-3,7-dimethyl-4a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[3,2-g]isoquinoline

Product 1

HCID 44331817(+/-)-trans-2-Diethylaminocarbonyl-3,7-dimethyl-4a-(3-hydroxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[3,2-g]isoquinolineYield 49.9%

Procedure

0.29 g (0.71 mmol) of (±)-trans-2-diethylaminocarbonyl-3,7-dimethyl-4a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[3,2-g]isoquinoline were treated with 0.4 ml (4.26 mmol) of boron tribromide as described in example 2. The residue was purified by flash chromatography (CH2Cl2 /MeOH/conc. NH4OH 80:12:0.8). The crude product was triturated with a mixture of acetone/MeOH=3:2, yielding 0.14 g of the title compound. M.p.=235°-238 l ° C.

Workup

  1. customThe residue was purified by flash chromatography (CH2Cl2 /MeOH/conc. NH4OH 80:12:0.8)
  2. customThe crude product was triturated with a mixture of acetone/MeOH=3:2

Sources & evidence

ORD record
ord-9bb3a9b9e5d04bb5b051c031681b6c2c
Source dataset
uspto-grants-1998_03
Patent number
US05731322

Reaction notes

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