Pyridine → 3-(4-Pyrrolidin-1-ylmethyl-phenyl)-propionaldehyde

HRID 1916528Notes

Reaction equation

HRID 1916528 reaction equation
N1C=CC=CC=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[N:29]1([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][CH2:43][OH:44])=[CH:37][CH:36]=2)[CH2:33][CH2:32][CH2:31][CH2:30]1>C(Cl)Cl>[N:29]1([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][CH:43]=[O:44])=[CH:37][CH:36]=2)[CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 159087TriacetoxyperiodinaneHCID 673653223-(4-Pyrrolidin-1-ylmethyl-phenyl)-propan-1-ol

Product 1

HCID 859698393-(4-Pyrrolidin-1-ylmethyl-phenyl)-propionaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.87 mL (35.56 mmol) pyridine and 2.11 g (4.98 mmol) Dess-Martin periodinane are added to a solution of 780 mg (3.56 mmol) 3-(4-pyrrolidin-1-ylmethyl-phenyl)-propan-1-ol in 30 mL DCM. The reaction mixture is stirred for 4 h at RT, then added to 100 mL saturated, aqueous NaHCO3 solution, exhaustively extracted with tert-butylmethylether, the organic phase is washed with saturated, aqueous NaCl solution and dried over Na2SO4. After the desiccant and solvent have been eliminated the crude product is further reacted without purification.

Workup

  1. additionadded to 100 mL saturated
  2. extractionaqueous NaHCO3 solution, exhaustively extracted with tert-butylmethylether
  3. washthe organic phase is washed with saturated, aqueous NaCl solution
  4. dry with materialdried over Na2SO4
  5. customis further reacted without purification

Sources & evidence

ORD record
ord-a106ba58e78a40e8ac93a8d745f53258
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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