Trimethylsilyl iodide → 1-(2-chlorophenyl)-5-[(1S,2S)-2-hydroxycyclohexyl]-2-(4-methoxyphenyl)-3-methyl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one

HRID 1790042ノート

反応式

HRID 1790042 の反応式
C([O:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[N:15]1[CH2:20][CH2:19][C:18]2[N:21]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:39])[C:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[C:23]([CH3:24])[C:17]=2[C:16]1=[O:40])C1C=CC=CC=1.C(O[C@H]1CCCC[C@@H]1N)C1C=CC=CC=1.ClC1C=CC=CC=1N1C2CCNCC=2C=C1C1C=CC(OC)=CC=1.C[Si](I)(C)C>C(Cl)Cl>[Cl:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[N:21]1[C:18]2[CH2:19][CH2:20][N:15]([C@H:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C@@H:9]3[OH:8])[C:16](=[O:40])[C:17]=2[C:23]([CH3:24])=[C:22]1[C:25]1[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=1

参加物

6

反応物 4

HCID 85247Trimethylsilyl iodideHCID 11908838(1S,2S)-trans-2-Benzyloxy-cyclohexylamineHCID 220385001-(2-chlorophenyl)-2-(4-methoxyphenyl)4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridineHCID 696641225-[(1S,2S)-2-(benzyloxy)cyclohexyl]-1-(2-chlorophenyl)-2-(4-methoxyphenyl)-3-methyl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one2 回

生成物 1

HCID 586651481-(2-chlorophenyl)-5-[(1S,2S)-2-hydroxycyclohexyl]-2-(4-methoxyphenyl)-3-methyl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one収率 24%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The starting material for this example, namely 5-[(1S,2S)-2-(benzyloxy)cyclohexyl]-1-(2-chlorophenyl)-2-(4-methoxyphenyl)-3-methyl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one, was prepared by following the methods described in Scheme 2 and Examples 12–19, using (1S,2S)-2-(benzyloxy)cyclohexylamine as R4NH2 (Scheme 2). Then, a sample of 5-[(1S,2S)-2-(benzyloxy)cyclohexyl]-1-(2-chlorophenyl)-2-(4-methoxyphenyl)-3-methyl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (200 mg, 0.36 mmol) was dissolved in methylene chloride (5 mL). Trimethylsilyl iodide (0.054 mL, 0.396 mmol) was added dropwise and the solution was stirred at rt for 18 h. The solvent was removed and the crude material was purified by silica gel column, eluting with methylene chloride followed by methanol. The product was isolated as a white solid (40.0 mg, 24%). LC-MS m/z (MH+) 465.3, retention time 3.23 min (method 1).

後処理

  1. customThe solvent was removed
  2. customthe crude material was purified by silica gel column
  3. washeluting with methylene chloride

出典と根拠

ORDレコード
ord-9d88810ec3fa46f2b9843685a10f101f
出典データセット
uspto-grants-2006_07
特許番号
US07071207B2

反応ノート

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