3-Methylbutanal → HCID 54421660, compound

HRID 1953912Notes

Reaction equation

HRID 1953912 reaction equation
[CH3:1][CH:2]([CH3:15])[CH2:3][C@H:4]([N:8]([CH3:14])[CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])[C:5]([OH:7])=[O:6].[CH:16](=O)[CH2:17][CH:18]([CH3:20])[CH3:19].[C:22](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:23].[Na+]>C(Cl)Cl>[CH2:19]([O:6][C:5](=[O:7])[C@@H:4]([N:8]([CH3:14])[CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])[CH2:3][CH:2]([CH3:15])[CH3:1])[C:18]1[CH:20]=[CH:23][CH:22]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 115523-MethylbutanalHCID 5049666Sodium triacetoxyborohydrideHCID 54343938HCID 54343938, compound

Product 1

HCID 54421660HCID 54421660, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Step 1: Method A of the synthesis of (S)-4-Methyl-2-[methyl-(3-methyl-butyl)-amino]-pentanoic acid (IIb) ##STR36## Step i: N-Methyl-O-benizyl-L-leucine p-tosylate salt (4.01 g, 9.84 mmol) was dissolved in CH2Cl2 (50 mL) and treated with isovaleraldehyde (1.06 mL, 9.84 mmol). The reaction was stirred at room temperature for 30 minutes and then cooled to 0° C. Sodium triacetoxyborohydride (3.13 g, 14.8 mmol) was added, and the reaction was allowed to warm to room temperature and stir overnight. The reaction was diluted with CH2Cl2 (400 mL). The organic layer was washed twice with saturated bicarbonate solution (2×400 mL), once with brine (400 mL), and then dried over Na2SO4. The solution was filtered, concentrated, and the crude material chromatographed on silica gel eluting with 10% EtOAc/hexanes to give 2.86 g (90%) of (S)-4-methyl-2-[methyl-(3-methyl-butyl)-amino]-pentanoic acid benzyl ester as a pale oil.

Workup

  1. temperaturecooled to 0° C
  2. temperatureto warm to room temperature
  3. stirringstir overnight
  4. washThe organic layer was washed twice with saturated bicarbonate solution (2×400 mL), once with brine (400 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationThe solution was filtered
  7. concentrationconcentrated
  8. customthe crude material chromatographed on silica gel eluting with 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-0e736e44782e422a8ba3a6d90d16e1e7
Source dataset
uspto-grants-2000_09
Patent number
US06117841

Reaction notes

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