Pyrrolidine → HCID 18403836, compound

HRID 1017678Notes

Reaction equation

HRID 1017678 reaction equation
[C:1]([CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH:8]=O)#[N:2].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:1]([CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH2:8][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14])#[N:2]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 2378268HCID 2378268, compoundHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18403836HCID 18403836, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 3-cyanomethoxy-4-methoxybenzaldehyde (10.0 g) in 1,2-dichloroethane (400 ml) was added pyrrolidine (6.6 ml), with stirring, followed by sodium triacetoxyborohydride (22 g). The reaction mixture was stirred at ambient temperature for 1 hr and poured into ice/water 10% sodium hydroxide solution. The mixture was extracted with ethyl acetate, washed with water, saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was dissolved in dichloromethane and high performance liquid chromatographed, eluting with dichloromethane, 1%, 2% and 5% methanol/dichloromethane. The appropriate fractions were collected and concentrated to give 8.7 g (63.5%) of product as an oil.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 1 hr
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with water, saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. dissolutionThe residue was dissolved in dichloromethane
  8. customhigh performance liquid chromatographed
  9. washeluting with dichloromethane, 1%, 2% and 5% methanol/dichloromethane
  10. customThe appropriate fractions were collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-72dc5bcca57e481980cd4c28e7663ca8
Source dataset
uspto-grants-2002_11
Patent number
US06479495B1

Reaction notes

Loading…