Pyrrolidine → HCID 86732730, compound

HRID 525863Notes

Reaction equation

HRID 525863 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:6][O:7][C:8]1[CH:29]=[CH:28][C:11]([CH2:12][O:13][C:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([CH:25]=O)[CH:21]=3)[N:16]([CH3:27])[CH:15]=2)=[CH:10][CH:9]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][O:13][C:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([CH2:25][N:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH:21]=3)[N:16]([CH3:27])[CH:15]=2)=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 86732728HCID 86732728, compound

Product 1

HCID 86732730HCID 86732730, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A solution of pyrrolidine (0.295 mL, 3.57 mmol) and 3-((4-methoxybenzyl)oxy)-1-methyl-4-oxo-1,4-dihydroquinoline-6-carbaldehyde (1.05 g, 3.25 mmol) in 1,2-dichloroethane (DCE) (50 mL) and 1 drop of acetic acid was treated with sodium triacetoxyborohydride (1.032 g, 4.87 mmol). The reaction mixture was stirred for 1.5 h, and was then concentrated under vacuum. The residue was taken in water (50 mL), and extracted with dichloromethane (2×50 mL). The organic layers were combined, washed with brine (50 mL), dried over sodium sulfate, and concentrated. The crude product was purified twice by automatic silica gel column chromatography (Combiflash RF), eluting with a mixture of [dichloromethane/methanol/ammonium hydroxide (80:20:2)]/dichlormethane (0-40%) to afford pure 3-((4-methoxybenzyl)oxy)-1-methyl-6-(pyrrolidin-1-ylmethyl)quinolin-4(1H)-one (1 g, 2.64 mmol, 81% yield) as a light yellow solid. LCMS: (M+H)+: 379.5.

Workup

  1. concentrationwas then concentrated under vacuum
  2. extractionextracted with dichloromethane (2×50 mL)
  3. washwashed with brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified twice by automatic silica gel column chromatography (Combiflash RF)
  7. washeluting with a mixture of [dichloromethane/methanol/ammonium hydroxide (80:20:2)]/dichlormethane (0-40%)

Sources & evidence

ORD record
ord-f5405720198e4bd2b93f658a22e270a0
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

Loading…