Diethylamine → HCID 58478769, compound

HRID 1254088Notes

Reaction equation

HRID 1254088 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[N:6][C:7]([CH:11]=O)=[CH:8][CH:9]=2)[CH2:4][O:3]1.[CH2:13]([NH:15][CH2:16][CH3:17])[CH3:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClC(Cl)C>[CH2:13]([N:15]([CH2:11][C:7]1[N:6]=[C:5]2[CH2:4][O:3][C:2](=[O:1])[C:10]2=[CH:9][CH:8]=1)[CH2:16][CH3:17])[CH3:14]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 58478784HCID 58478784, compound

Product 1

HCID 58478769HCID 58478769, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 5-oxo-5,7-dihydro-furo[3,4-b]pyridine-2-carbaldehyde (110 mg, 0.68 mmol) in dichloroethane (4 mL) is treated with diethylamine (75 μL, 0.68 mmol) followed by the addition of sodium triacetoxyborohydride (200 mg, 0.94 mmol). The reaction mixture is stirred at room temperature for 1.5 h. and then treated with saturated aqueous NaHCO3 solution. The aqueous layer is extracted twice with EtOAc (2×). The combined organic extracts are dried, and concentrated. The residue is chromatographed (silica gel, EtOAc/hexane). The product containing fractions are concentrated to give the title compound as white solid (90 mg, 61%).

Workup

  1. extractionThe aqueous layer is extracted twice with EtOAc (2×)
  2. customThe combined organic extracts are dried
  3. concentrationconcentrated
  4. customThe residue is chromatographed (silica gel, EtOAc/hexane)
  5. additionThe product containing fractions
  6. concentrationare concentrated

Sources & evidence

ORD record
ord-b3cf457dea624d988b9a3c4f49571a9c
Source dataset
uspto-grants-2013_06
Patent number
US08455535B2

Reaction notes

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