Diphenylsilane → Methyl (R)-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline-6-carboxylate

HRID 1875328

반응식

HRID 1875328 반응식
[CH3:1][N:2]1[C@H:11]([CH3:12])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13]([O:15][CH3:16])=[O:14])[CH:8]=2)[C:3]1=O.C1([SiH2]C2C=CC=CC=2)C=CC=CC=1>C1COCC1.[C-]#[O+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Rh]>[CH3:1][N:2]1[C@H:11]([CH3:12])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13]([O:15][CH3:16])=[O:14])[CH:8]=2)[CH2:3]1

참가 물질

5

반응물 2

HCID 69888Diphenylsilane2회HCID 86761672methyl (R)-2,3-dimethyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-6-carboxylate

생성물 1

HCID 86761671Methyl (R)-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline-6-carboxylate

시약·촉매·용매 2

HCID 10941995Carbonylhydridotris(triphenylphosphine)rhodium(I)촉매2회HCID 8028Tetrahydrofuran용매

실험 절차

60 mg (257 μmol) methyl (R)-2,3-dimethyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-6-carboxylate are dissolved in 2 ml THF under an argon atmosphere and at RT combined with 100 μl (542 μmol) diphenylsilane. Then 20 mg (21 μmol) carbonylhydridotris(triphenylphosphine)rhodium(I) are added and the mixture is stirred for two hours. A further 50 μl diphenylsilane and 10 mg carbonylhydridotris(triphenylphosphine)rhodium(I) are added and the mixture is stirred for a further 2.5 hours. Then the reaction mixture is evaporated down i. vac. and purified by flash chromatography on silica gel (eluant DCM/MeOH 95:5).

후처리

  1. stirringthe mixture is stirred for a further 2.5 hours
  2. customThen the reaction mixture is evaporated down i
  3. customand purified by flash chromatography on silica gel (eluant DCM/MeOH 95:5)

출처 및 근거

ORD 기록
ord-aecf0787748f46eabe57a4dd91f97eba
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309542B2

연결된 노트

불러오는 중…