Isobutyraldehyde → HCID 86646581, compound

HRID 2080553Notes

Reaction equation

HRID 2080553 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][CH2:11][S:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[CH:22](=O)[CH:23]([CH3:25])[CH3:24].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].S([O-])([O-])(=O)=O.[Mg+2]>ClCCCl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:10][CH2:11][S:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6561IsobutyraldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5049666Sodium triacetoxyborohydrideHCID 86646582HCID 86646582, compound

Product 1

HCID 86646581HCID 86646581, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

This compound was made in a manner analogous to that set forth in Step A of Example 3, using 2.0 grams (0.0062 mole) of [(6-chloro(3-pyridyl))methyl]{2-[(4-methoxyphenyl)methylthio]ethyl}-amine, 0.45 gram (0.0062 mole) of isobutyraldehyde, 2.0 gram (0.0093 mole) of sodium triacetoxyborohydride and 1.5 grams (0.0124 mole) of magnesium sulfate in 40 mL of 1,2-dichloroethane. The yield of the subject compound after one column chromatography purification on silica gel, eluting with a mixture of ethyl acetate and hexanes, was 2.05 grams. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThe yield of the subject compound after one column chromatography purification on silica gel
  2. washeluting with a mixture of ethyl acetate and hexanes

Sources & evidence

ORD record
ord-123cf99f777941cfa21c16cf510baad6
Source dataset
uspto-grants-2011_04
Patent number
US07932393B2

Reaction notes

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