Chlorotrimethylsilane → HCID 57941061, compound

HRID 1437365Notes

Reaction equation

HRID 1437365 reaction equation
C([Mg]CCCC)CCC.[CH3:10][Si:11](Cl)([CH3:13])[CH3:12].CC1N(C(N(C)C)=O)C1.[CH2:24]([O:26][C:27]([CH:29]1[CH2:34][CH2:33][C:32](=[O:35])[CH2:31][CH2:30]1)=[O:28])[CH3:25].C(=O)([O-])O.[Na+]>C1COCC1.CCCCCCC.CCCCCC.O>[CH2:24]([O:26][C:27]([C@@H:29]1[CH2:34][CH2:33][C:32]([O:35][Si:11]([CH3:13])([CH3:12])[CH3:10])=[CH:31][CH2:30]1)=[O:28])[CH3:25]

Participants

10

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 516892Sodium BicarbonateHCID 11007919N,N,2-trimethylaziridine-1-carboxamideHCID 178448196HCID 178448196, compound

Product 1

HCID 57941061HCID 57941061, compoundYield 80%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8900HeptaneSolvent

Conditions

Temperature
-78 °C

Procedure

To (S,S)-bis α-methyl benzylamine (9 g, 40 mmol) in THF (200 mL) under argon was added dibutyl magnesium in heptane (20 mL, 1M) and the mixture heated to reflux. After 1.5 hours, the mixture was cooled to −78° C. and trimethylsilyl chloride (10.1 mL) and N,N-dimethylpropyleneurea (1.2 mL) added dropwise. After a further 20 minutes ethyl-4-oxocyclohexane carboxylate (2.87 mL, 18 mmol) was added dropwise. The reaction was stirred at −78° C. for 16 hours, then saturated sodium hydrogen carbonate (100 mL), water (100 mL) and hexane (200 mL) were added. The organic soluble material was purified by chromatography on silica gel eluting with 0-5% diethyl ether in hexane to give an oil (3.5 g, 80%).

Workup

  1. temperaturethe mixture heated to reflux
  2. customThe organic soluble material was purified by chromatography on silica gel eluting with 0-5% diethyl ether in hexane

Sources & evidence

ORD record
ord-878009f017c84059a98c0d0bf96be9e5
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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