Acetic Acid → HCID 86723759, compound

HRID 577530Notes

Reaction equation

HRID 577530 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH:12]([CH3:14])[CH3:13])[C:5]([CH3:10])=[C:6]([CH:9]=1)[CH:7]=O.[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18][NH2:19].[BH3-]C#N.[Na+].CC(O)=O>CO>[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH:12]([CH3:14])[CH3:13])[C:5]([CH3:10])=[C:6]([CH:9]=1)[CH2:7][NH:19][CH2:18][CH:17]([O:20][CH3:21])[O:16][CH3:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 89728Aminoacetaldehyde dimethyl acetalHCID 5003444Sodium cyanoborohydrideHCID 86723758HCID 86723758, compound

Product 1

HCID 86723759HCID 86723759, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-bromo-2-methyl-3-(propan-2-yloxy)benzaldehyde (108b, 4.5 g, 18 mmol) and 2,2-dimethoxyethanamine (2.2 g, 21 mmol) in MeOH (50 mL) was added NaBH3CN (1.4 g, 22 mmol) and HOAc (1 mL) at 0° C. The reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with water (50 mL). The reaction mixture was concentrated under vacuum. The residue was extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine (2×30 mL), dried over Na2SO4, filtered, and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc=5:1) to obtain N-[5-bromo-2-methyl-3-(propan-2-yloxy)benzyl]-2,2-dimethoxyethanamine (108c, 3.5 g, 58%) as a colorless oil.

Workup

  1. customThe reaction mixture was quenched with water (50 mL)
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. extractionThe residue was extracted with EtOAc (3×30 mL)
  4. washThe combined organic layers were washed with brine (2×30 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by column chromatography (petroleum ether/EtOAc=5:1)

Sources & evidence

ORD record
ord-e5f9088d8c7c49fb8f563e61064221bd
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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