Sodium Bicarbonate → HCID 59177295, compound

HRID 2076801Notes

Reaction equation

HRID 2076801 reaction equation
[C:1]1([C@@H:7]2[O:12][CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13][C:14]1[N:19]=[CH:18][C:17]([CH:20]=O)=[CH:16][CH:15]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClC(Cl)C>[Cl:13][C:14]1[N:19]=[CH:18][C:17]([CH2:20][N:9]2[CH2:10][CH2:11][O:12][C@@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8]2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 937783(2S)-2-PhenylmorpholineHCID 27640536-Chloropyridine-3-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 59177295HCID 59177295, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

10 g of (S)-2-Phenyl-morpholine was dissolved in 610 mL of dichloroethane. 10.407 g of 6-Chloropyridine-3-carboxaldehyde was added and the reaction stirred at room temperature for 30 minutes followed by addition of 23.4 g of sodium triacetoxyborohydride. After stirring overnight at room temperature, the solution was poured into an aqueous saturated sodium bicarbonate solution and the layers separated. The organic layer was washed several times with aqueous saturated sodium bicarbonate solution followed by brine. It was then dried over sodium sulfate, filtered and concentrated in vacuo. Purification was accomplished by flash chromatography to afford 11.23 g of product. 63.5% yield. EI m/z 289=MH+

Workup

  1. stirringAfter stirring overnight at room temperature
  2. customthe layers separated
  3. washThe organic layer was washed several times with aqueous saturated sodium bicarbonate solution
  4. dry with materialIt was then dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification

Sources & evidence

ORD record
ord-42d9c266a6524a7caaa7d7da320ac266
Source dataset
uspto-grants-2011_04
Patent number
US07928103B2

Reaction notes

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