Pivalaldehyde → HCID 57507327, compound

HRID 556497Notes

Reaction equation

HRID 556497 reaction equation
[CH3:1][C:2]([CH3:6])([CH3:5])[CH:3]=O.[CH3:7][O:8][C:9](=[O:13])[CH2:10][CH2:11][NH2:12].[BH3-]C#N.[Na+]>CO>[CH3:7][O:8][C:9](=[O:13])[CH2:10][CH2:11][NH:12][CH2:3][C:2]([CH3:6])([CH3:5])[CH3:1]

Participants

5

Reactant 3

HCID 12417PivalaldehydeHCID 192794Methyl beta-alanateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 57507327HCID 57507327, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.5 g 2,2-Dimethyl-propionaldehyde, 2.18 g 3-Amino-propionic acid methyl ester and 50 ml MeOH was stirred at room temperature for 30 min. 1.5 g NaCNBH3 was added in small portion. The mixture was stirred for another 3 hrs. The solvent was removed in vacuum. 50 mL Water was added to the residue and the mixture was basified to PH10 by 1N NaOH. The solution was extracted by EtOAc (30 mL×3). The organic phase was washed by 20 mL water, dried over Na2SO4. Removed the solvent gave 0.66 g target molecule as clear oil.

Workup

  1. stirringThe mixture was stirred for another 3 hrs
  2. customThe solvent was removed in vacuum
  3. addition50 mL Water was added to the residue
  4. extractionThe solution was extracted by EtOAc (30 mL×3)
  5. washThe organic phase was washed by 20 mL water
  6. dry with materialdried over Na2SO4
  7. customRemoved the solvent
  8. customgave 0.66 g target molecule as clear oil

Sources & evidence

ORD record
ord-68a5da71205a4c94ac7c77eac94ea6bf
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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