Potassium Carbonate → 5-(Cyclopropyl-methyl-amino)-2-ethynyl-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalene

HRID 1870013Notes

Reaction equation

HRID 1870013 reaction equation
[CH:1]1([N:4]([CH:6]2[C:15]3[C:10](=[CH:11][C:12]([C:16]#[C:17][Si](C)(C)C)=[CH:13][CH:14]=3)[C:9]([CH3:23])([CH3:22])[CH2:8][CH2:7]2)[CH3:5])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH:1]1([N:4]([CH:6]2[C:15]3[C:10](=[CH:11][C:12]([C:16]#[CH:17])=[CH:13][CH:14]=3)[C:9]([CH3:23])([CH3:22])[CH2:8][CH2:7]2)[CH3:5])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57424267Cyclopropyl-(4,4-dimethyl-6-trimethylsilanylethynyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-methyl-amine2×

Product 1

HCID 211071955-(Cyclopropyl-methyl-amino)-2-ethynyl-8,8-dimethyl-5,6,7,8-tetrahydro-naphthaleneYield 75.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of cyclopropyl-(4,4-dimethyl-6-trimethylsilanylethynyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-methyl-amine (Intermediate 167, 0.67 g, 2.62 mmol) in methanol (10 mL) was treated with potassium carbonate (1 g, 7.23 mmol) and the resulting reaction mixture was stirred at ambient temperature overnight. The volatiles were evaporated in vacuo and the residue was diluted with water and extracted with diethyl ether. The organic extract was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product as a light yellow oil (0.5 g, 75%).

Workup

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo
  3. additionthe residue was diluted with water
  4. extractionextracted with diethyl ether
  5. extractionThe organic extract
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-6b30ca477dc744e5b0f21348b88fcac8
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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