2,4-Dimethoxybenzaldehyde → HCID 66874912, compound

HRID 249916Notes

Reaction equation

HRID 249916 reaction equation
[NH:1]1[C@@H:10]2[C@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[NH:4][CH2:3][C:2]1=[O:11].[CH3:12][O:13][C:14]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:15]=1[CH:16]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>CC(O)=O.C(Cl)Cl>[CH3:12][O:13][C:14]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:15]=1[CH2:16][N:4]1[C@@H:5]2[C@H:10]([CH2:9][CH2:8][CH2:7][CH2:6]2)[NH:1][C:2](=[O:11])[CH2:3]1

Participants

7

Reactant 4

HCID 691752,4-DimethoxybenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 21796269HCID 21796269, compound

Product 1

HCID 66874912HCID 66874912, compoundYield 11.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (4aS,8aS)-octahydroquinoxalin-2(1H)-one (8.82 g, 57.19 mmol), 2,4-dimethoxybenzaldehyde (9.50 g, 57.19 mmol), and sodium triacetoxyborohydride (36.31 g, 171.57 mmol) in 1% HOAc in CH2Cl2 (250 mL) was stirred at room temperature for 16 h. The mixture was neutralized with saturated aqueous NaHCO3 solution (200 mL). The organic layer was separated and washed with H2O (100 mL), brine (100 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel, 0% to 100% 90:9:1 CH2Cl2/CH3OH/NH4OH in CH2Cl2) afforded (4aS,8aS)-4-(2,4-dimethoxybenzyl)octahydroquinoxalin-2(1H)-one (1.10 g, 11.1% over two steps). 1H NMR and MS consistent.

Workup

  1. customThe organic layer was separated
  2. washwashed with H2O (100 mL), brine (100 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue by column chromatography (silica gel, 0% to 100% 90:9:1 CH2Cl2/CH3OH/NH4OH in CH2Cl2)

Sources & evidence

ORD record
ord-09f85068a51949dc853d9382c286082e
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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