Benzyl succinimido carbonate → Benzyl 4-(ethyl(methyl)amino)-2-methylbutan-2-ylcarbamate

HRID 2061098Notes

Reaction equation

HRID 2061098 reaction equation
[CH2:1]([N:3]([CH3:10])[CH2:4][CH2:5][C:6]([CH3:9])([NH2:8])[CH3:7])[CH3:2].[C:11](ON1C(=O)CCC1=O)([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]>C1COCC1>[CH2:1]([N:3]([CH3:10])[CH2:4][CH2:5][C:6]([NH:8][C:11](=[O:12])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:9])[CH3:7])[CH3:2]

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 60134549N1-Ethyl-N1,3-dimethylbutane-1,3-diamine

Product 1

HCID 60134505Benzyl 4-(ethyl(methyl)amino)-2-methylbutan-2-ylcarbamateYield 55.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Crude N1-ethyl-N1,3-dimethylbutane-1,3-diamine (1.87 g, 12.9 mmol) was dissolved into THF (100 mL) and cooled in an ice bath. Solid CbzOSu (3.23 g, 1 equiv, 12.9 mmol) was added to the reaction in one portion. The reaction was left to stir at room temperature for 16 h. The solvent was removed and the residue was taken up in a mixture of ethyl acetate (150 mL) and water (50 mL). The layers were separated and the organic layer washed with 1 M sodium carbonate (2×50 mL) and brine (50 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated to a pale yellow oil (3.29 g). The crude oil was purified on an ISCO purification system with gradient elution from 15 to 100% ethyl acetate in hexanes. The desired fractions were collected and concentrated to give a pale yellow oil (1.81 g, yield: 55.5%). 1H NMR (CDCl3, 400 MHz): δ 1.05-1.09 (t, J=8, 3H), 1.38 (s, 6H), 1.64-1.67 (t, J=6, 2H), 2.22 (s, 3H), 2.39-2.44 (q, J=6.6, 2H), 2.46-2.49 (t, J=6, 2H), 5.07 (s, 2H), 7.16 (bs, 1H), 7.28-7.41 (m, 5H). LRMS (ESI+) for C16H26N2O2 (278.2); Found: 279 (MH+).

Workup

  1. temperaturecooled in an ice bath
  2. waitThe reaction was left
  3. customThe solvent was removed
  4. additionthe residue was taken up in a mixture of ethyl acetate (150 mL) and water (50 mL)
  5. customThe layers were separated
  6. washthe organic layer washed with 1 M sodium carbonate (2×50 mL) and brine (50 mL)
  7. dry with materialThe organic layer was dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to a pale yellow oil (3.29 g)
  10. customThe crude oil was purified on an ISCO purification system with gradient elution from 15 to 100% ethyl acetate in hexanes
  11. customThe desired fractions were collected
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-dfbac0497f6f4e3eaf1a92b62b600b0f
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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