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

HRID 1770703Notes

Reaction equation

HRID 1770703 reaction equation
[CH2:1]([O:8][C:9]([O:11]N1C(=O)CCC1=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][C:20]([NH2:27])([CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[CH3:21]>O1CCCC1>[CH3:25][N:24]([CH3:26])[CH2:23][CH2:22][C:20]([NH:27][C:9](=[O:11])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=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 69.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(Benzyloxycarbonyloxy)succinimide (15.6 g, 1 equiv, 62.6 mmol) was added in one portion to a solution of N1,N1-3-trimethylbutane-1,3-diamine (8.15 g, 62.6 mmol) in tetrahydrofuran (100 mL). The reaction was left to stir at room temperature for 17 hours. 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 by flash chromatography (1% to 5% methanol in dichloromethane). 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/APCI) m/z 265 [M+H]+.

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 by flash chromatography (1% to 5% methanol in dichloromethane)
  10. customThe desired fractions were collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-044838a1628e4d5a99b0a4bfe048811e
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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