반응 #2962

ord-9bb3a9b9e5d04bb5b051c031681b6c2c

반응 방정식

CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@]1(c3cccc(OC)c3)CCN(C)C[C@@H]1C2
(±)-trans-2-diethylaminocarbonyl-3,7-dimethyl-4a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[3,2-g]isoquinoline
BrB(Br)Br
boron tribromide
CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@]1(c3cccc(O)c3)CCN(C)C[C@@H]1C2
title compound
수율 49.9%
CCN(CC)C(=O)c1[nH]c2c(c1C)C[C@@]1(c3cccc(O)c3)CCN(C)C[C@@H]1C2
(±)-trans-2-Diethylaminocarbonyl-3,7-dimethyl-4a-(3-hydroxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[3,2-g]isoquinoline
수율 49.9%

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

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

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05731322uspto-grants-1998_03