Methyl iodide → HCID 57424240, compound

HRID 1869908Notes

Reaction equation

HRID 1869908 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:22]=[C:21]([CH:23]=[CH2:24])[C:20]3[C:19](=O)[CH2:18][CH2:17][C:16]([CH3:27])([CH3:26])[C:15]=3[CH:14]=2)=[CH:7][CH:6]=1.[CH:29]1([NH2:32])[CH2:31][CH2:30]1.[C:33]([BH3-])#N.[Na+].C(=O)([O-])[O-].[K+].[K+].CI>ClCCl.C(#N)C.O.C(=O)(O)[O-].[Na+].C(OCC)C.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:22]=[C:21]([CH:23]=[CH2:24])[C:20]3[CH:19]([N:32]([CH:29]4[CH2:31][CH2:30]4)[CH3:33])[CH2:18][CH2:17][C:16]([CH3:27])([CH3:26])[C:15]=3[CH:14]=2)=[CH:7][CH:6]=1

Participants

12

Reactant 5

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 57424239HCID 57424239, compound2×

Product 1

HCID 57424240HCID 57424240, compoundYield 60%

Reagents, catalysts & solvents 6

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of [4-(8,8-dimethyl-5-oxo-4-vinyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-phenyl]-acetic acid methyl ester (Intermediate 70, 0.205 g, 0.55 mmol) in dichloromethane (4 mL) and acetonitrile (2 mL) was treated with cyclopropyl amine (1 mL, 14.45 mmol). After 5 minutes, acetic acid (1 mL) was added followed by sodium cyanoborohydride (0.138 g, 2.2 mmol). The reaction mixture was stirred overnight at ambient temperature. It was then diluted with water and saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to an oil. The oil was dissolved in acetone (10 mL) and treated with potassium carbonate (0.227 g, 1.65 mmol) followed by methyl iodide (0.54 mL, 8.7 mmol) and the resulting reaction mixture was stirred overnight at ambient temperature. Diethyl ether was added to the reaction mixture and the precipitated solids were filtered off, the filtrate was evaporated in vacuo to a residue. Flash column chromatography over silica gel (230-400 mesh) using 4-5% ethyl acetate in hexane as the eluent afforded the title compound (0.14 g, 60%).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe combined organic extract
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo to an oil
  6. dissolutionThe oil was dissolved in acetone (10 mL)
  7. customthe resulting reaction mixture
  8. stirringwas stirred overnight at ambient temperature
  9. filtrationthe precipitated solids were filtered off
  10. customthe filtrate was evaporated in vacuo to a residue

Sources & evidence

ORD record
ord-d27be90cc1524fd48105455eb5c3b093
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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