Triacetoxyperiodinane → Benzyl 3-formylpiperidine-1-carboxylate

HRID 48474

Reaction equation

HRID 48474 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([CH2:17][OH:18])[CH2:12]1)=[O:10])[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]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH:17]=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 6932120benzyl (3R)-3-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 9899653Benzyl 3-formylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring, 0° C. solution of 0.303 g (1.20 mmol) of 3-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester (8) in CH2Cl2 (4.0 mL) was added 0.630 g (1.44 mmol) of Dess-Martin periodinane, and the solution was stirred under N2. When the reaction was complete by TLC (about 30 min.), the reaction was concentrated, and then Et2O was added. After standing for about 15 min., the reaction was filtered through Celite wet with Et2O, rinsed with Et2O, and concentrated. The crude reaction was purified by column chromatography (florisil®, 100-200 mesh, 2:1 Hexane: EtOAc) to achieve pure 9.

Workup

  1. customwas complete by TLC (about 30 min.)
  2. concentrationthe reaction was concentrated
  3. additionEt2O was added
  4. filtrationthe reaction was filtered through Celite wet with Et2O
  5. washrinsed with Et2O
  6. concentrationconcentrated
  7. customThe crude reaction
  8. customwas purified by column chromatography (florisil®, 100-200 mesh, 2:1 Hexane: EtOAc)

Sources & evidence

ORD record
ord-b2a037f8cccc4e88ae1cfed235e1c2c0
Source dataset
uspto-grants-2004_03
Patent number
US06703508B2

Linked notes

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