Dimethylformamide → 4-[2-(6-Benzyloxy-3-methyl-1H-indol-5-yl)-2-oxo-ethyl]-piperazine-1-carboxylic acid benzyl ester

HRID 1433162

반응식

HRID 1433162 반응식
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:21](=[O:24])[CH2:22]Br)=[C:10]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:11]=2)[C:6]([CH3:25])=[CH:5]1)(=O)C.C([O-])([O-])=O.[K+].[K+].[C:32]([N:42]1[CH2:47][CH2:46]C[CH2:44][CH2:43]1)([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33].C[N:49](C=O)C>>[CH2:35]([O:34][C:32]([N:42]1[CH2:43][CH2:44][N:49]([CH2:22][C:21]([C:9]2[CH:8]=[C:7]3[C:12](=[CH:11][C:10]=2[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH:4][CH:5]=[C:6]3[CH3:25])=[O:24])[CH2:46][CH2:47]1)=[O:33])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 228749Benzyl piperidine-1-carboxylateHCID 579348421-(1-Acetyl-6-benzyloxy-3-methyl-1H-indol-5-yl)-2-bromo-ethanone

생성물 1

HCID 579348164-[2-(6-Benzyloxy-3-methyl-1H-indol-5-yl)-2-oxo-ethyl]-piperazine-1-carboxylic acid benzyl ester수율 17%

실험 절차

Compound 1-(1-acetyl-6-benzyloxy-3-methyl-1H-indol-5-yl)-2-bromo-ethanone (0.039 g, 0.1 mmol), K2CO3 (0.019 g, 0.14 mmol) and Cbz-piperidine (0.026 ml, 0.1 mmol) was stirred in DMF (2 ml) at room temperature for 5 hours. The solvent was removed in vacuo and the residue redissolved in DCM and washed with water, brine, dried over MgSO4. Purification by column chromatography in hexane/EtOAc (3:2) afforded the product (0.008 g, 17%). LC/MS: RT=2.236 min. 498 (MH+).

후처리

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue redissolved in DCM
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. customPurification by column chromatography in hexane/EtOAc (3:2)

출처 및 근거

ORD 기록
ord-31d29dae79dc4d77b5a0dbc62178d1a6
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612201B2

연결된 노트

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