Ethyl oxoacetate → HCID 66941718, compound

HRID 2106508Notes

Reaction equation

HRID 2106508 reaction equation
[CH3:1][C:2]1([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.O=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C1COCC1>[CH2:26]([O:25][C:23]([CH2:22][N:5]1[CH2:6][CH2:7][C:2]([N:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]2)([CH3:1])[CH2:3][CH2:4]1)=[O:24])[CH3:27]

Participants

6

Reactant 4

HCID 70211Ethyl oxoacetateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 66941891HCID 66941891, compound

Product 1

HCID 66941718HCID 66941718, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.53 g (4.78 mmol) tert-butyl 4-(4-methyl-piperidin-4-yl)-piperazine-1-carboxylate and 1.1 mL (5.55 mmol) ethyl oxo-acetate (50% in toluene) in 50 mL THF was stirred for 1 h at RT. The reaction mixture was cooled to 0° C., 1.25 g (5.90 mmol) sodium triacetoxyborohydride was added batchwise and after elimination of the cooling bath the mixture was stirred overnight at RT. It was combined with 10 mL 20% NaHCO3 solution, extracted exhaustively with EtOAc and the combined organic phases were dried over Na2SO4. After elimination of the desiccant and solvent the residue was purified by chromatography (Alox, DCM/EtOH 100:1).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringafter elimination of the cooling bath the mixture was stirred overnight at RT
  3. extractionextracted exhaustively with EtOAc
  4. dry with materialthe combined organic phases were dried over Na2SO4
  5. customAfter elimination of the desiccant and solvent the residue was purified by chromatography (Alox, DCM/EtOH 100:1)

Sources & evidence

ORD record
ord-8fd5c68af2c84930b8586d1403c35d7a
Source dataset
uspto-grants-2009_08
Patent number
US07579341B2

Reaction notes

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