Sodium Iodide → tert-butyl (3S)-3-methyl-4-[6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl]piperazine-1-carboxylate

HRID 1191914ノート

反応式

HRID 1191914 の反応式
Cl[CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=2)[CH2:4][CH2:3]1.[CH3:15][C@@H:16]1[NH:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]1.[I-].[Na+].C(N(CC)CC)C>CN(C=O)C.O>[CH3:15][C@@H:16]1[N:21]([CH:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=3)[CH2:4][CH2:3]2)[CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:17]1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 7023035(S)-1-Boc-3-methylpiperazineHCID 592126531-Chloro-6-(trifluoromethyl)indane

生成物 1

HCID 59212635tert-butyl (3S)-3-methyl-4-[6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl]piperazine-1-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 1-chloro-6-(trifluoromethyl)indane (1.52 g, 6.89 mmol), tert-butyl (3S)-3-methylpiperazine-1-carboxylate (2.1 g, 10 mmol), sodium iodide (3 g, 20 mmol) and triethylamine (3 g, 30 mmol) in DMF (20 mL) was stirred at 60° C. overnight. After cooling to room temperature, water was added. The resulting solution was extracted with EtOAc twice. The combined extracts were washed with water and brine, dried over MgSO4 and concentrated. Column chromatography on silica (10%-30% EtOAc in hexane) afforded two isomers. Isomer 1: 0.52 g (brown oil). MS calculated for C20H27F3N2O2: (M+H)+ 385. found 385.2. Isomer 2: 0.41 g (brown oil). MS: (M+H)+ 385.2

後処理

  1. extractionThe resulting solution was extracted with EtOAc twice
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customColumn chromatography on silica (10%-30% EtOAc in hexane) afforded two isomers

出典と根拠

ORDレコード
ord-91c9c8eba6ef4407a195b2efa27aac61
出典データセット
uspto-grants-2014_03
特許番号
US08680104B2

反応ノート

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