Triethylamine → 1-Boc-piperidine-3-carboxaldehyde

HRID 535860Notes

Reaction equation

HRID 535860 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][OH:15])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C>CS(C)=O>[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH:14]=[O:15])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 2763851tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 99644481-Boc-piperidine-3-carboxaldehydeYield 68.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

1-BOC-3-hydroxymethylpiperidine (2.15 g, 10 mmol) and triethylamine (3.03 g, 30 mmol) were dissolved in 10 mL DMSO, 15 mL DMSO solution of SO3Py (4.77 g, 30 mmol) was added to the above mixture in dropwise and the result mixture was stirred at rt for 2 hrs. The mixture was poured into 100 mL ice-water, extracted with EtOAc (100 mL×3), organic layer was washed with brine, dried with Na2SO4, filtered, and the filtrate was evaporated in vacuo. The crude product was purified by chromatography on silica gel (PE/EtOAc 5:1) to give 1.46 g product as colorless oil (68.5%). 1H NMR (300 MHz, CDCl3) δ: 9.70 (1H, s), 3.91-3.93 (1H, m), 3.62-3.67 (1H, m), 3.29-3.36 (1H, m), 3.05-3.13 (1H, m), 2.40-2.45 (1H, m), 1.95-1.97 (1H, m), 1.63-1.72 (1H, m), 1.49-1.59 (1H, m), 1.46 (9H, s).

Workup

  1. extractionextracted with EtOAc (100 mL×3), organic layer
  2. washwas washed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. customthe filtrate was evaporated in vacuo
  6. customThe crude product was purified by chromatography on silica gel (PE/EtOAc 5:1)

Sources & evidence

ORD record
ord-ff213587786a479a892298a356d60870
Source dataset
uspto-grants-2014_10
Patent number
US08859553B2

Reaction notes

Loading…