Trimethylsilyldiazomethane → HCID 178514372, compound

HRID 535622Notes

Reaction equation

HRID 535622 reaction equation
[N+:1](=[CH:3][Si](C)(C)C)=[N-:2].[CH2:8]1[C@@H:13]2[CH2:14][C:15]3([C:17](Cl)=[O:18])[CH2:16][C@H:9]1[CH2:10][CH:11]3[CH2:12]2>CCOCC.C(#N)C.C1COCC1.CCOC(C)=O>[CH2:8]1[CH:9]2[CH2:16][C:15]3([C:17]([O-:18])=[CH:3][N+:1]#[N:2])[CH2:14][CH:13]1[CH2:12][CH:11]3[CH2:10]2

Participants

7

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 111269552,5-Methanopentalene-3a(1H)-carbonyl chloride, hexahydro- (9CI)

Product 1

HCID 178514372HCID 178514372, compoundYield 108.1%

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (diazomethyl)trimethylsilane (2.70 mL, 5.40 mmol) in Et2O was added to a solution of 3-noradamantanecarbonyl chloride (0.495 g, 2.68 mmol) in acetonitrile (4 mL) and THF (4 mL), stirred at room temperature overnight, diluted with EtOAc, washed with water and brine, dried (Na2SO4), filtered, and concentrated to give 551 mg of crude title compound as a yellow solid: MS (APCI+) M/Z 191 (M+H)+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d3b55fd3e2654004a71e31f11eb41bd8
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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