Methyl chloroformate → HCID 86751880, compound

HRID 725780Notes

Reaction equation

HRID 725780 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([N:15]1[CH2:20][CH:19]3[CH2:21][CH:16]1[CH2:17][NH:18]3)(=[O:14])=[O:13])=[CH:7]2.CCCCC[CH2:27][CH3:28].ClC(OC)=[O:31]>O1CCOCC1.[OH-].[Na+]>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([N:15]1[CH2:20][CH:19]3[CH2:21][CH:16]1[CH2:17][N:18]3[C:27]([CH3:28])=[O:31])(=[O:13])=[O:14])=[CH:7]2

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 8900HeptaneHCID 19708705HCID 19708705, compound

Product 1

HCID 86751880HCID 86751880, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared from 2-(5-Chloro-2-naphthylsulfonyl)-2,5-diazabicyclo[2.2.1]heptane, by dissolving the heptane (0.29 g, 0.8 mmol) in 20 ml dioxane and 1 ml of 1N NaOH solution. The solution was cooled with an ice bath. Methyl chloroformate (0.062 ml, 0.8 mmol) was added dropwise. Additional 1N NaOH solution was added to keep the pH above 9. After 1 hour at room temperature, the solvent was evaporated. The residue was partitioned between chloroform and saturated sodium bicarbonate solution. The aqueous layer was extracted three times with chloroform. After drying over magnesium sulfate, the solvent was evaporated to give a yellow foam. This was purified by chromatotron using 3/2 hexane/ethyl acetate to give 0.27 g (87% yield) of a white solid: mp 151°-152° C.; 1H NMR (CDCl3): 8.41-8-37 (m, 2 H, H1 and H3), 7.95-7-89 (m, 2 H, H4 and H6), 7.71 (d, J=7.4, 1 H, H8), 7.53 (t, J=7.8, 1 H, H7), 4.58 (s, 1 H, alkyl H), 4.49 (s, 1 H, alkyl H), 3.68 (s, 1 H, alkyl H), 3.55-3.46 (m, 4 H, alkyl H's), 1.70 (d, J=10.1, 1 H, alkyl H), 1.33-1.28 (m, 1 H, alkyl H).

Workup

  1. temperatureThe solution was cooled with an ice bath
  2. customthe solvent was evaporated
  3. customThe residue was partitioned between chloroform and saturated sodium bicarbonate solution
  4. extractionThe aqueous layer was extracted three times with chloroform
  5. dry with materialAfter drying over magnesium sulfate
  6. customthe solvent was evaporated
  7. customto give a yellow foam
  8. customThis was purified by chromatotron

Sources & evidence

ORD record
ord-045219ddce994b0d8f3638748a0a1dd3
Source dataset
uspto-grants-1998_01
Patent number
US05707985

Reaction notes

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