Ethyl Acetate → 2-Cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline-6-carbaldehyde

HRID 1935783Notes

Reaction equation

HRID 1935783 reaction equation
[CH:1]1([N:4]2[CH2:13][C:12]([CH3:15])([CH3:14])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([CH2:16][OH:17])[CH:10]=3)[CH2:5]2)[CH2:3][CH2:2]1.C[N+]1([O-])CCOCC1.C(OCC)(=O)C>ClCCl.C(#N)C.CCCCCC.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH:1]1([N:4]2[CH2:13][C:12]([CH3:14])([CH3:15])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([CH:16]=[O:17])[CH:10]=3)[CH2:5]2)[CH2:3][CH2:2]1

Participants

8

Reactant 3

HCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 225688112-Cyclopropyl-6-hydroxymethyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline2×

Product 1

HCID 225689542-Cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline-6-carbaldehydeYield 37%

Reagents, catalysts & solvents 4

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent2×

Procedure

A solution of 2-cyclopropyl-6-hydroxymethyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline (Intermediate 24, 0.74 g, 3.2 mmol) in dichloromethane (10 mL) and acetonitrile (2.5 mL) was treated sequentially with 4A° molecular sieves powder (1.06 g), tetra-n-propyl ammonium perruthenate (0.050 g, 0.14 mmol) and N-methyl morpholine N-oxide (1.1 g, 9.8 mmol). After stirring at ambient temperature for 0.5 h, it was diluted with 5 mL of hexane and subjected to flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent to afford the title compound as an oil (0.27 g, 37%).

Sources & evidence

ORD record
ord-4f341d967d2f43679aa292a0cc4f2a63
Source dataset
uspto-grants-2002_05
Patent number
US06387892B1

Reaction notes

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