Potassium Carbonate → HCID 66942072, compound

HRID 2106512Notes

Reaction equation

HRID 2106512 reaction equation
O=[C:2]1[CH2:8][CH:7]2[N:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:4]([CH2:5][CH2:6]2)[CH2:3]1.[N:17]1([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[K+].[K+]>C1COCC1.CC(O)=O>[CH2:26]([O:25][C:23]([N:17]1[CH2:22][CH2:21][N:20]([CH:2]2[CH2:8][CH:7]3[N:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:4]([CH2:5][CH2:6]3)[CH2:3]2)[CH2:19][CH2:18]1)=[O:24])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 643495Benzyl piperazine-1-carboxylateHCID 2794767tert-Butyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 66942072HCID 66942072, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5.00 g (22.2 mmol) tert-butyl 3-oxo-8-aza-bicyclo[3.2.1]octan-8-carboxylate and benzyl piperazine-1-carboxylate in 60 mL THF was adjusted with AcOH to a pH of 5 and stirred for 1 h at RT. The mixture was combined batchwise with 5.64 g (26.6 mmol) sodium triacetoxyborohydride while cooling with ice and the reaction mixture was stirred overnight at RT. It was combined with 150 mL 15% K2CO3 solution, the organic phase was separated off, the aqueous phase was exhaustively extracted with EtOAc and the combined organic phases were dried over Na2SO4. After elimination of the desiccant and solvent the residue was purified by chromatography (silica gel, EtOAc).

Workup

  1. temperaturewhile cooling with ice
  2. stirringthe reaction mixture was stirred overnight at RT
  3. customthe organic phase was separated off
  4. extractionthe aqueous phase was exhaustively extracted with EtOAc
  5. dry with materialthe combined organic phases were dried over Na2SO4
  6. customAfter elimination of the desiccant and solvent the residue was purified by chromatography (silica gel, EtOAc)

Sources & evidence

ORD record
ord-bdf7857f58974594b5c8b9ae1693b323
Source dataset
uspto-grants-2009_08
Patent number
US07579341B2

Reaction notes

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