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

HRID 1875328

Reaction equation

HRID 1875328 reaction equation
[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

Participants

5

Reactant 2

HCID 69888Diphenylsilane2×HCID 86761672methyl (R)-2,3-dimethyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-6-carboxylate

Product 1

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

Reagents, catalysts & solvents 2

HCID 10941995Carbonylhydridotris(triphenylphosphine)rhodium(I)Catalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-aecf0787748f46eabe57a4dd91f97eba
Source dataset
uspto-grants-2012_11
Patent number
US08309542B2

Linked notes

Loading…