Methyl chloroformate → HCID 22630125, compound

HRID 2307078Notes

Reaction equation

HRID 2307078 reaction equation
Cl.[CH3:2][C:3]1([CH3:14])[CH2:8][C:7]([CH3:10])([CH3:9])[CH2:6][C:5]([CH:12]=[CH2:13])([NH2:11])[CH2:4]1.C([O-])([O-])=O.[Na+].[Na+].Cl[C:22]([O:24][CH3:25])=[O:23]>C1COCC1.C(OCC)C>[CH3:2][C:3]1([CH3:14])[CH2:8][C:7]([CH3:9])([CH3:10])[CH2:6][C:5]([NH:11][C:22](=[O:23])[O:24][CH3:25])([CH:12]=[CH2:13])[CH2:4]1

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 10340Sodium CarbonateHCID 226301351-Ethenyl-3,3,5,5-tetramethylcyclohexan-1-amine--hydrogen chloride (1/1)

Product 1

HCID 22630125HCID 22630125, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of amine hydrochloride 5 (0.25 g, 1.2 mmol) and Na2CO3 (0.73 g, 6.9 mmol) in THF (6 ml) was stirred at room temperature for 1 h. Methyl chloroformate (0.27 ml, 3.45 mmol) was added and the reaction mixture was stirred at room temperature for 15 h. The mixture was diluted with diethyl ether (20 ml), filtered and evaporated to the dryness. The crude product was purified by flash chromatography on silica gel (light petroleum ether-ethyl acetate, 10:1) to give 6 (0.24 g, 87%) as a colorless solid with m.p. 61-63° C. 1H-NMR (CDCl3, TMS): 0.92 and 1.15 (total 12H, both s, 3,5-CH3); 1.00-1.40 (4H, m, 4-CH2 and 2,6-CH); 2.00 (2H, d, 14 Hz, 2,6-CH); 3.62 (3H, s, CH3N); 4.72 (1H, br s, NH); 5.00 and 5.06 (total 2H, both d, 10.5 and 17 Hz, ═CH2) and 5.83 ppm (1H, dd, 10.5 and 17 Hz, ═CH).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 15 h
  2. filtrationfiltered
  3. customevaporated to the dryness
  4. customThe crude product was purified by flash chromatography on silica gel (light petroleum ether-ethyl acetate, 10:1)

Sources & evidence

ORD record
ord-44bfb58cf0b5439eb819b5e33419c32a
Source dataset
uspto-grants-2004_12
Patent number
US06828462B2

Reaction notes

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