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

HRID 1433162

反応式

HRID 1433162 の反応式
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

参加物

5

反応物 4

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

生成物 1

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

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-31d29dae79dc4d77b5a0dbc62178d1a6
出典データセット
uspto-grants-2009_11
特許番号
US07612201B2

関連ノート

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