Triacetoxyperiodinane → (S)-2-(benzylcarbonylamino)-propionaldehyde

HRID 132125Notes

Reaction equation

HRID 132125 reaction equation
[CH2:1]([C:8]([NH:10][C@@H:11]([CH3:14])[CH2:12][OH:13])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH2:1]([C:8]([NH:10][C@@H:11]([CH3:14])[CH:12]=[O:13])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 28345725(S)-2-(benzylcarbonylamino)-propanol

Product 1

HCID 86595334(S)-2-(benzylcarbonylamino)-propionaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-2-(benzylcarbonylamino)-propanol (5 g, 23.9 mmol) was dissolved in CH2Cl2 (200 mL) and treated with Dess-Martin periodinane (12.26 g, 1.1 eq). The mixture was stirred for 2 hours, then quenched with sodium thiosulphate, and the solvent removed in vacuo. The residue was then separated between sodium hydroxide (1M, 500 mL) and ethyl acetate (500 mL). The organics were washed with brine, dried (MgSO4) and evaporated in vacuo to yield a clear oil which was used immediately in the next step without further purification.

Workup

  1. customquenched with sodium thiosulphate
  2. customthe solvent removed in vacuo
  3. customThe residue was then separated between sodium hydroxide (1M, 500 mL) and ethyl acetate (500 mL)
  4. washThe organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customto yield a clear oil which
  8. customwas used immediately in the next step without further purification

Sources & evidence

ORD record
ord-6056ccb5fb754a1d81e9d378b7a73d24
Source dataset
uspto-grants-2008_06
Patent number
US07384970B2

Reaction notes

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