2-Pyridinecarboxaldehyde → HCID 178448296, compound

HRID 1964788Notes

Reaction equation

HRID 1964788 reaction equation
[O-]S([O-])(=O)=O.[Mg+2].[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]=O.[NH2:15][C@H:16]([CH:19]([CH3:21])[CH3:20])[CH2:17][OH:18]>C(Cl)Cl>[CH3:20][CH:19]([CH3:21])[C@@H:16](/[N:15]=[CH:13]/[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][N:7]=1)[CH2:17][OH:18]

Participants

5

Reactant 3

HCID 142732-PyridinecarboxaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 6950587D-Valinol

Product 1

HCID 178448296HCID 178448296, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Anhydrous MgSO4 (50 g, 415 mmol, 4.15 eq) and a substituted aryl or heteroaryl carboxaldehyde, e.g. 2-pyridinecarboxaldehyde (9.5 ml, 100 mmol, 1 eq), were added to a solution of (R)-(−)-2-amino-3-methyl-1-butanol (10.32 g, 100 mmol) in dry DCM (150 ml) at 0° C. The reaction was followed by LC/MS. The mixture was stirred at this temperature for 2 h 25. MgSO4 was filtered off and the DCM removed by evaporation to give the desired product (XVIII*), e.g. (2R)-3-methyl-2-{[(E)-2-pyridinylmethylidene]amino}-1-butanol as a yellowish oil (19.23 g, quantitative yield).

Workup

  1. filtrationMgSO4 was filtered off
  2. customthe DCM removed by evaporation

Sources & evidence

ORD record
ord-13746ffd2cc84a8c80ce83e10cfddf3a
Source dataset
uspto-grants-2013_04
Patent number
US08415480B2

Reaction notes

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