Benzyl succinimido carbonate → HCID 178511686, compound

HRID 1420309Notes

Reaction equation

HRID 1420309 reaction equation
[C@H:1]1([NH2:8])[CH2:6][CH2:5][C@H:4]([NH2:7])[CH2:3][CH2:2]1.[C:9]1([CH2:15][O:16][C:17](ON2C(=O)CCC2=O)=[O:18])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCOCC1>[NH3:7].[C:9]1([CH2:15][O:16][C:17](=[O:18])[NH:7][C@H:4]2[CH2:5][CH2:6][C@H:1]([NH2:8])[CH2:2][CH2:3]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 178511674HCID 178511674, compound

Product 2

HCID 222AmmoniaHCID 178511686HCID 178511686, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of trans 1,4-cyclohexanediamine (22.8 g, 200 mmol) in dry dioxan (100 ml) was cooled to 5°-10° and treated dropwise with 1-[[(phenylmethoxy)carbonyl]oxy]-2,5-pyrrolidinedione (4.98 g, 20 mmol) in dioxan (50 ml) over 3 h. The mixture was warmed to 21° then stirred for a further 2 h and filtered. The filtrate was evaporated to give a solid which was purified on silica eluted with dichloromethane:ethanol:0.88 ammonia (30:8:1) to give the title compound (2.58 g) as a white solid. MH+ =249.

Workup

  1. temperatureThe mixture was warmed to 21°
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. customto give a solid which
  5. customwas purified on silica
  6. washeluted with dichloromethane

Sources & evidence

ORD record
ord-3422dc6bfbda4e4e961e2383d11f41b0
Source dataset
uspto-grants-1999_03
Patent number
US05889178

Reaction notes

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