Water → HCID 22626865, compound

HRID 277895Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:17][C:16]([CH3:19])([CH3:18])[C:15]2[C:10](=[CH:11][CH:12]=[C:13](OS(C(F)(F)F)(=O)=O)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[CH3:29][N:30](C)C=O>[C-]#N.[Zn+2].[C-]#N>[C:1]([O:5][C:6]([N:8]1[CH2:17][C:16]([CH3:19])([CH3:18])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:29]#[N:30])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

Tetrakis (triphenylphosphine)palladium (0) (4.10 g, 0.0035 mol) was added to a suspension of N-tert-butyloxycarbonyl-4,4-dimethyl-6-trifluoromethylsulfonyloxy-1,2,3,4-tetrahydroisoquinoline (36.37 g, 0.089 mol) and zinc cyanide (10.44 g, 0.089 mol) in anhydrous dimethyl formamide (280 ml) under argon. The resultant was heated at 100° C. for 4 hours, cooled and poured into water (800 ml). The mixture was filtered through kieselguhr and the filter cake washed with ethyl acetate. The bilayered filtrate was separated and the aqueous layer extracted into ethyl acetate (4×500 ml). Combined organics were washed with water (3×250 ml), brine (250 ml), dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica gel using 0-15 % ethyl acetate in hexane gradient elution to afford the title compound as a colourless oil (21.75 g, 85%).

Workup

temperaturecooled
filtrationThe mixture was filtered through kieselguhr
washthe filter cake washed with ethyl acetate
customThe bilayered filtrate was separated
extractionthe aqueous layer extracted into ethyl acetate (4×500 ml)
washCombined organics were washed with water (3×250 ml), brine (250 ml)
dry with materialdried (Na2SO4)
customevaporated in vacuo
customThe residue was chromatographed on silica gel using 0-15 % ethyl acetate in hexane gradient elution

Sources & evidence

ORD record: ord-440213d2553347f391172f8b3f63a507
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06358974B1

Reaction notes

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