Potassium Iodide → (+/-)-trans-2-Cyclopropylmethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride

HRID 2857

反応式

HRID 2857 の反応式
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C@@:10]23[CH2:19][C:18](=[O:20])[CH2:17][CH2:16][C@H:15]2[CH2:14][NH:13][CH2:12][CH2:11]3)[CH:7]=[CH:8][CH:9]=1.[CH:21]1([CH2:24]Br)[CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[ClH:1].[CH:21]1([CH2:24][N:13]2[CH2:12][CH2:11][C@@:10]3([C:6]4[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH3:2])[CH:5]=4)[C@@H:15]([CH2:16][CH2:17][C:18](=[O:20])[CH2:19]3)[CH2:14]2)[CH2:23][CH2:22]1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 86752321(+/-)-trans-4a-(3-Methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8, 8a-decahydroisoquinoline hydrochloride

生成物 1

HCID 86752322(+/-)-trans-2-Cyclopropylmethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride収率 26%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

0.88 g (3.08 mmol) of (±)-trans-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 0.44 g (3,23 mmol) of cyclopropylmethyl bromide, 0.64 g of potassium carbonate and a catalytical amount of potassium iodide in 15.4 ml of DMF were stirred at 60° C. for 2 h. The solvent was removed in vacuo, and the crude product was purified by flash chromatography (EtOAc/MeOH/conc. NH4OH 90:10:0.8). The solid product was dissolved in acetone and the solution brought to acidic pH with HCl/Et2O. The precipitate was filtered, yielding 0.28 g of the title compound. M.p.=78° C. dec.

後処理

  1. customThe solvent was removed in vacuo
  2. customthe crude product was purified by flash chromatography (EtOAc/MeOH/conc. NH4OH 90:10:0.8)
  3. dissolutionThe solid product was dissolved in acetone
  4. filtrationThe precipitate was filtered

出典と根拠

ORDレコード
ord-d8b6f19e1cf843a08f290872c0b51286
出典データセット
uspto-grants-1998_03
特許番号
US05731322

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