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

HRID 1191914노트

반응식

HRID 1191914 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-91c9c8eba6ef4407a195b2efa27aac61
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680104B2

반응 노트

불러오는 중…