Sodium Carbonate → Methyl 4-{[(benzyloxy)carbonyl]amino}bicyclo[2.2.2]octane-1-carboxylate

HRID 1969602Notes

Reaction equation

HRID 1969602 reaction equation
Cl.[NH2:2][C:3]12[CH2:10][CH2:9][C:6]([C:11]([O:13][CH3:14])=[O:12])([CH2:7][CH2:8]1)[CH2:5][CH2:4]2.C([O-])([O-])=O.[Na+].[Na+].[C:21](=O)([O:30]N1C(=O)CCC1=O)[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCOCC1.O.CCOC(C)=O>[CH2:23]([O:22][C:21]([NH:2][C:3]12[CH2:4][CH2:5][C:6]([C:11]([O:13][CH3:14])=[O:12])([CH2:9][CH2:10]1)[CH2:7][CH2:8]2)=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 83172Benzyl succinimido carbonateHCID 67216420Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate hydrochloride

Product 1

HCID 23149677Methyl 4-{[(benzyloxy)carbonyl]amino}bicyclo[2.2.2]octane-1-carboxylateYield 100.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate hydrochloride (1.16 g, 5.29 mmol, Prime Organics) in 1,4-dioxane (15 mL) was added a solution of Na2CO3 (0.90 g, 8.49 mmol) in water (15 mL). The reaction mixture was stirred for about 5 min at ambient temperature. Benzyl 2,5-dioxopyrrolidin-1-yl carbonate (1.32 g, 5.29 mmol) was added and the reaction mixture was stirred at ambient temperature for about 72 h. The reaction mixture was diluted with EtOAc (50 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×20 mL). The combined organic layers were dried over anhydrous MgSO4, filtered, and concd under reduced pressure to give methyl 4-(benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylate (1.68 g, 95%): LC/MS (Table 1, Method a) Rt=2.44 min; MS m/z: 318 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for about 72 h
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (2×20 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-1cdc91fcd26a472cac76f0f4b4fae8fb
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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