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 1790042노트

반응식

HRID 1790042 반응식
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

참가 물질

6

반응물 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-one2회

생성물 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-one수율 24%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-9d88810ec3fa46f2b9843685a10f101f
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071207B2

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