Bis(2-Methoxyethyl)amine → Benzyl(4-(bis(2-methoxyethyl)amino)-2-methylbutan-2-yl)carbamate

HRID 1056356Notes

Reaction equation

HRID 1056356 reaction equation
[CH2:1]([O:8][C:9](=[O:17])[NH:10][C:11]([CH3:16])([CH2:13][CH:14]=O)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][O:19][CH2:20][CH2:21][NH:22][CH2:23][CH2:24][O:25][CH3:26].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.CC(O)=O>[CH2:1]([O:8][C:9](=[O:17])[NH:10][C:11]([CH3:16])([CH2:13][CH2:14][N:22]([CH2:23][CH2:24][O:25][CH3:26])[CH2:21][CH2:20][O:19][CH3:18])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 2383Bis(2-Methoxyethyl)amineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 15473343benzyl N-(1,1-dimethyl-3-oxo-propyl)carbamate

Product 1

HCID 89793752Benzyl(4-(bis(2-methoxyethyl)amino)-2-methylbutan-2-yl)carbamateYield 66.1%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

To a 100-mL round-bottomed flask was added benzyl(2-methyl-4-oxobutan-2-yl)carbamate (1.04 g, 4.42 mmol) and bis(2-methoxyethyl)amine (0.776 mL, 5.30 mmol, Sigma-Aldrich) in 1,2-dichloroethane (20 mL) followed by AcOH (0.3 mL). The mixture was stirred at RT for 10 min, then sodium triacetoxyborohydride (1.124 g, 5.30 mmol, Sigma-Aldrich) was added portion wise. The reaction was stirred at RT for 1 h. Sat. NaHCO3 (20 mL) was added slowly and the mixture was extracted with EtOAc (40 mL×3). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified with silica gel chromatography (eluted with 10-90% EtOAc in Hex) to give benzyl(4-(bis(2-methoxyethyl)amino)-2-methylbutan-2-yl)carbamate (1.03 g, 2.92 mmol, 66% yield) as a colorless oil. MS (ESI, pos. ion) m/z: 353.1 (M+1); 1H NMR (400 MHz, CDCl3) δ ppm 7.27-7.40 (5H, m), 6.94 (1H, br. s.), 5.05 (2H, s), 3.45 (4H, t, J=5.8 Hz), 3.26 (6H, s), 2.64-2.73 (6H, m), 1.62 (2H, t, J=6.4 Hz), 1.36 (6H, s).

Workup

  1. stirringThe reaction was stirred at RT for 1 h
  2. extractionthe mixture was extracted with EtOAc (40 mL×3)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified with silica gel chromatography (eluted with 10-90% EtOAc in Hex)

Sources & evidence

ORD record
ord-2143cc90c71d4894aed01e5c797400e9
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…