Glutaraldehyde → HCID 86695044, compound

HRID 1053591Notes

Reaction equation

HRID 1053591 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][CH2:8][N:9]([CH2:16][CH3:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH:20](=O)[CH2:21][CH2:22][CH2:23][CH:24]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:16]([N:9]([CH2:8][CH2:7][O:6][C:5]1[CH:4]=[CH:3][C:2]([N:1]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:17]

Participants

5

Reactant 3

HCID 3485GlutaraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 28300823HCID 28300823, compound

Product 1

HCID 86695044HCID 86695044, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Compound 20 (120 mg, 0.47 mmol) and glutaraldehyde (46 mg, 0.23 mmol) was dissolved in 10 mL 1,2-dichloroethane and sodium triacetoxyborohydride (400 mg, 1.89 mmol) was added portionwise over 6 hrs and reaction was stirred overnight. The reaction was quenched with sat. sodium carbonate, extracted with EtOAc (2×25 mL), washed with water and then brine and dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography provide the compound 22 (55 mg, 0.17 mmol, 36% yield). 1H NMR (CDCl3, 400 MHz) δ 7.23-7.28 (m, 2H), 6.68-6.94 (m, 7H), 4.10 (t, J=6.4 Hz, 2H), 3.72 (t, J=6.4 Hz, 2H), 3.50 (q, J=7.2 Hz, 2H), 3.05 (t, J=5.6 Hz, 4H), 1.72-1.78 (m, 4H), 1.54-1.60 (m, 2H), 1.22 (t, J=6.8 Hz, 3H); HRMS (ESI, positive) m/z calcd. for C21H29N2O [M+H]+: 325.2280, found: 325.2227.

Workup

  1. customreaction
  2. customThe reaction was quenched with sat. sodium carbonate
  3. extractionextracted with EtOAc (2×25 mL)
  4. washwashed with water
  5. dry with materialbrine and dried over Na2SO4
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1349fbf0d33b4eceacad64bd0718a809
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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