Triethylamine → HCID 69622402, compound

HRID 1743726Notes

Reaction equation

HRID 1743726 reaction equation
[CH:1]12[N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:5]([CH2:6][CH2:7]1)[CH2:4][NH:3][CH2:2]2.C(N(CC)CC)C.[CH2:23]([O:30][C:31](ON1C(=O)CCC1=O)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)(Cl)Cl>[CH:1]12[N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:31]([O:30][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:32])[CH2:2]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 157409088-Boc-3,8-diaza-bicyclo(3.2.1)octane

Product 1

HCID 69622402HCID 69622402, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Conditions

Temperature
0 °C

Procedure

tert-Butyl 3,8-diazabicyclo[3.2.1]octane-8-carboxylate (7.0 g, 33.0 mmol; from Preparation B above) and triethylamine (6.8 mL, 36 mmol) were dissolved in CHCl3 (80 mL) and cooled to 0° C. N-(Benzyloxycarbonyloxy)succinimide (9.0 g, 36.1 mmol), dissolved in CHCl3 (70 mL), was slowly added 0° C. The solution was allowed to reach r.t, and was stirred at r.t overnight. CHCl3 (200 mL) was added and the solution was washed with water, then dried and evaporated. The residue was then dissolved in ether and washed with 2 M HCl in order to remove any remaining unreacted starting material. Drying and evaporation gave 10 g (88%) of the sub-title compound.

Workup

  1. customwas slowly added 0° C
  2. washthe solution was washed with water
  3. customdried
  4. customevaporated
  5. dissolutionThe residue was then dissolved in ether
  6. washwashed with 2 M HCl in order
  7. customto remove any remaining
  8. customDrying
  9. customevaporation

Sources & evidence

ORD record
ord-9af40fab357041ac9ba9e14ed7311c88
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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