2-Methylquinoline → 2-Methyl-1,2,3,4-tetrahydroquinoline

HRID 515861

반응식

HRID 515861 반응식
N1CCC[C@@H]1C(N)=O.C(N(CC)CC)C.[CH3:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1.C(O)=O.C(N(CC)CC)C>C(Cl)Cl.C[Ir-4](Cl)(C)(C)(C)(C)C1C=CC=C1.[Ir](Cl)(Cl)Cl>[CH3:16][CH:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18]1

참가 물질

8

반응물 4

HCID 70602-MethylquinolineHCID 8471TriethylamineHCID 447554Prolinamide, D-HCID 11084032Triethylammonium formate

생성물 1

HCID 962892-Methyl-1,2,3,4-tetrahydroquinoline수율 67.4%

시약·촉매·용매 3

HCID 25563Iridium trichloride촉매HCID 178477776HCID 178477776, 화합물촉매HCID 6344Dichloromethane용매2회

실험 절차

To 10 ml of methylene chloride, 55.6 mg of a pentamethylcyclopentadienyl iridium(III) chloride dimer ([Cp*IrCl2]2), 16.7 mg of (R)-prolinamide and 15.6 mg of triethylamine were added, and the mixture was stirred under argon atmosphere at room temperature for about 30 minutes to give a catalyst-containing mixture. In 60 ml of methylene chloride, 1.00 g of 2-methylquinoline was dissolved, and a 1/10 amount of the catalyst-containing mixture (equivalent to 0.1 mol % as an iridium chloride dimer) was added. After cooling to −10° C., 8.4 ml of a mixed solvent of formic acid/triethylamine (molar ratio: 5/2) was added dropwise, and the mixture was stirred at the same temperature for 2 days to give 2-methyl-1,2,3,4-tetrahydroquinoline (degree of conversion: 67.4%). The R-enantiomer was in excess and the optical purity was 85.4% ee.

후처리

  1. customto give a catalyst-containing mixture
  2. temperatureAfter cooling to −10° C.
  3. stirringthe mixture was stirred at the same temperature for 2 days

출처 및 근거

ORD 기록
ord-575810ee10444fc9bf54261a52ea2d01
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108986B2

연결된 노트

불러오는 중…