Benzyl succinimido carbonate → Benzyl 4-(dimethylamino)-2-methylbutan-2-ylcarbamate

HRID 2061036Notes

Reaction equation

HRID 2061036 reaction equation
[C:1]([O:11]N1C(=O)CCC1=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[CH3:19][C:20]([NH2:27])([CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[CH3:21]>C1COCC1>[CH3:25][N:24]([CH3:26])[CH2:23][CH2:22][C:20]([NH:27][C:1](=[O:11])[O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)([CH3:21])[CH3:19]

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 22743653N~1~,N~1~,3-Trimethylbutane-1,3-diamine

Product 1

HCID 60134454Benzyl 4-(dimethylamino)-2-methylbutan-2-ylcarbamateYield 89.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Solid CbzOSu (15.6 g, 1 equiv, 48.8 mmol) was added in one portion to a solution of N1,N1-3-trimethylbutane-1,3-diamine (8.15 g, 62.6 mmol) in THF (100 mL). The reaction was left to stir at room temperature for 17 h. The solvent was removed and the residue was taken up in a mixture of ethyl acetate (500 mL) and water (100 mL). The layers were separated and the organic layer washed with saturated sodium bicarbonate (2×100 mL), water (100 mL) and brine (100 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated to a pale yellow oil. The crude oil was purified on an ISCO purification system with gradient elution from 1-5% methanol in DCM. The desired fractions were collected and concentrated to give a colorless oil (11.49 g, yield: 69.6%). 1H NMR (CDCl3, 400 MHz): δ 1.35 (s, 6H), 1.67-1.72 (t, J=6.6, 2H), 2.23 (s, 6H), 2.36-2.40 (t, J=7.2, 2H), 6.46 (s, 1H), 7.27-7.36 (m, 5H), LRMS (ESI+) for C15H24N2O2 (264.2); Found: 265 (MH+).

Workup

  1. waitThe reaction was left
  2. customThe solvent was removed
  3. additionthe residue was taken up in a mixture of ethyl acetate (500 mL) and water (100 mL)
  4. customThe layers were separated
  5. washthe organic layer washed with saturated sodium bicarbonate (2×100 mL), water (100 mL) and brine (100 mL)
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to a pale yellow oil
  9. customThe crude oil was purified on an ISCO purification system with gradient elution from 1-5% methanol in DCM
  10. customThe desired fractions were collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-ab08e096665c4173b1ed23b0dd88edb2
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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