tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylate → 1-Boc-piperidine-3-carboxaldehyde

HRID 1839178Notes

Reaction equation

HRID 1839178 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[C:12]([N:19]1[CH2:24][CH2:23][CH2:22][CH:21]([CH2:25][OH:26])[CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>C(Cl)Cl>[C:12]([N:19]1[CH2:24][CH2:23][CH2:22][CH:21]([CH:25]=[O:26])[CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 2763851tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylateHCID 178418287HCID 178418287, compound

Product 1

HCID 99644481-Boc-piperidine-3-carboxaldehydeYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of pyridinium chlorochromate (98%, 34.0 g, 0.155 mol) and Celite (24 g) in 200 mL of dry CH2Cl2 was added N-Boc-3-piperidinemethanol (2) (22.15 g, 0.103 mol) in 30 mL of CH2Cl2 in one portion, and the mixture was stirred at room temperature overnight. The mixture was filtered by passing through a funnel filled with 20 g of Celite. After the solvent was removed, the remaining oily residue was purified by a flash column (silica gel; hexane:ethyl acetate, 4:1) to afford 3 as a colorless oil 17.5 g (80%).

Workup

  1. filtrationThe mixture was filtered
  2. customby passing through a funnel
  3. additionfilled with 20 g of Celite
  4. customAfter the solvent was removed
  5. customthe remaining oily residue was purified by a flash column (silica gel; hexane:ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-707a4839eeaf495caa0c3dfec04a7ecf
Source dataset
uspto-grants-2004_01
Patent number
US06677332B1

Reaction notes

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