Methyl iodide → 1-(Methyl-iso-propylamino)-4,4-dimethyl-6-trimethylsilanylethynyl-1,2,3,4-tetrahydro-naphthalene

HRID 844650Notes

Reaction equation

HRID 844650 reaction equation
[CH3:1][C:2]1([CH3:19])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[C:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:10]=2)[CH2:5][C:4](=O)[CH2:3]1.[CH:20]([NH2:23])([CH3:22])[CH3:21].[C:24](=O)([O-])[O-].[K+].[K+].CI>CCCCCC.CC1(C)C2C(=CC=C(C#C[Si](C)(C)C)C=2)CC(=O)C1.C([BH3-])#N.[Na+].C(OCC)(=O)C.CC(C)=O.C(O)(=O)C.C(#N)C.ClCCl>[CH:20]([N:23]([CH3:24])[CH:5]1[C:6]2[C:11](=[CH:10][C:9]([C:12]#[C:13][Si:14]([CH3:17])([CH3:16])[CH3:15])=[CH:8][CH:7]=2)[C:2]([CH3:19])([CH3:1])[CH2:3][CH2:4]1)([CH3:22])[CH3:21]

Participants

13

Reactant 4

HCID 6328Methyl iodideHCID 6363IsopropylamineHCID 11430Potassium CarbonateHCID 22568874HCID 22568874, compound

Product 1

HCID 225688201-(Methyl-iso-propylamino)-4,4-dimethyl-6-trimethylsilanylethynyl-1,2,3,4-tetrahydro-naphthaleneYield 95%

Reagents, catalysts & solvents 8

HCID 5003444Sodium cyanoborohydrideCatalystHCID 22568874HCID 22568874, compoundCatalystHCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following general procedure G and using a solution of 4,4-dimethyl-6-trimethylsilanylethynyl-1,2,3,4-tetrahydro-naphthalene 2-one (Intermediate 12, 0.2 g, 0.78 mmol), dichloromethane (4 mL), acetonitrile (2 mL), acetic acid (1 mL), isopropyl amine (1 mL, 11.74 mmol) and sodium cyanoborohydride (0.19 g, 3.02 mmol), after 15days of reaction time and work up afforded an intermediate (0. 14 g, 60%, 0.47 mmol) which was used following general procedure H along; with acetone (2 mL), potassium carbonate (0.6 g, 4.34 mmol) and methyl iodide (0.5 mL, 8 mmol). The crude product after work up was subjected to flash column chromatography over silica gel (230-400 mesh) using 15% ethyl acetate in hexane as the eluent to afford the title compound as a pale yellow oil (D.14 g, 95%).

Workup

  1. customafter 15days of reaction time and work
  2. customup afforded an intermediate (0. 14 g, 60%, 0.47 mmol) which

Sources & evidence

ORD record
ord-89cc55351d6647cab29790068dcb58a1
Source dataset
uspto-grants-2002_04
Patent number
US06380256B1

Reaction notes

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