Cerium(III) chloride → N,N-diethyl-2-hydroxy-2-(3-hydroxymethyl-2-oxo-1,2-dihydro-pyridin-4-yl)-butyramide

HRID 30491

Reaction equation

HRID 30491 reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[C:4]([C:6]1([CH2:17][CH3:18])[C:14]2[CH:13]=[CH:12][NH:11][C:10](=[O:15])[C:9]=2[C:8](=[O:16])[O:7]1)=[O:5])[CH3:2].C(OC(=O)C(N(CC)CC)=O)C.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+].C(=O)([O-])O.[Na+].[Cl-].[Na+].O>C(O)C>[CH2:19]([N:3]([CH2:1][CH3:2])[C:4](=[O:5])[C:6]([OH:7])([C:14]1[CH:13]=[CH:12][NH:11][C:10](=[O:15])[C:9]=1[CH2:8][OH:16])[CH2:17][CH3:18])[CH3:20]

Participants

7

Reactant 5

HCID 24636Cerium(III) chlorideHCID 138489Ethyl N,N-diethyloxamateHCID 4311764Sodium borohydrideHCID 674550481-Ethyl-3,4-dioxo-1,3,4,5-tetrahydro-furo[3,4-c]pyridine-1-carboxylic acid diethylarnideHCID 129703874Sodium hydrogencarbonate brine

Product 1

HCID 45141716N,N-diethyl-2-hydroxy-2-(3-hydroxymethyl-2-oxo-1,2-dihydro-pyridin-4-yl)-butyramideYield 61.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
15 °C

Procedure

To a solution of 1.000 g of compound (14) as obtained from example 8 (3.595 mmol) in 40 mL ethanol were added at room temperature 2.215 g cerium (III) chloride (grinded, 8.99 mmol, 2.5 eq). The suspension was placed in an ultrasonic bath for 10 min and was then cooled to 15° C. by a water bath. 2.40 g sodium borohydride (61.1 mmol, 17 eq) were added in 6 portions over 3 h. After additional 2 h at room temperature, the suspension was poured onto 800 mL saturated aqueous sodium hydrogencarbonate/brine (1:1) and the mixture was vigorously stirred for 13 h prior to extraction with five times 400 mL, dichloromethane/ethanol (4:1). The combined organic extracts were evaporated in a rotary evaporator (50° C., 5 mbar). The crude product was obtained as a purple-red solid (879.6 mg, 87% by weight), which was purified by trituration with 5.25 mL dichloromethane/methyl tert-butyl ether (2:1) yielding the title compound (623.2 mg, 2.21 mmol, 61% by weight) as a white solid.

Workup

  1. waitAfter additional 2 h at room temperature
  2. extractionto extraction with five times 400 mL, dichloromethane/ethanol (4:1)
  3. customThe combined organic extracts were evaporated in a rotary evaporator (50° C., 5 mbar)
  4. customThe crude product was obtained as a purple-red solid (879.6 mg, 87% by weight), which
  5. customwas purified by trituration with 5.25 mL dichloromethane/methyl tert-butyl ether (2:1)

Sources & evidence

ORD record
ord-e081bff47d5d4c34a5ecae1d63611658
Source dataset
uspto-grants-2008_09
Patent number
US07423152B2

Linked notes

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