Benzyl succinimido carbonate → Benzyl 1-(dimethylamino)-2-methylpropan-2-ylcarbamate

HRID 2061033Notes

Reaction equation

HRID 2061033 reaction equation
[CH3:1][N:2]([CH3:8])[CH2:3][C:4]([CH3:7])([NH2:6])[CH3:5].[C:9](ON1C(=O)CCC1=O)([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]>C(O)(C)C.O>[CH3:1][N:2]([CH3:8])[CH2:3][C:4]([NH:6][C:9](=[O:10])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:7])[CH3:5]

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 226843(2-Amino-2-methylpropyl)dimethylamine

Product 1

HCID 60134495Benzyl 1-(dimethylamino)-2-methylpropan-2-ylcarbamateYield 73.3%

Reagents, catalysts & solvents 1

HCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

N1,N1,2-Trimethylpropane-1,2-diamine (5.68 g, 48.8 mmol) was dissolved into isopropanol/water (1:1, 150 mL). To this solution was added CbzOSu (12.2 g, 1 equiv, 48.8 mmol) in one portion. The reaction was left to stir at room temperature overnight for 17 h. The solvent was removed and the residue was taken up in a mixture of ethyl acetate (300 mL) and water (100 mL). The layers were separated and the organic layer extracted with water (2×100 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated to an oil. The crude oil was purified on an ISCO purification system with gradient elution from 2% methanol in DCM to 30% methanol in DCM. The desired fraction was collected and concentrated to give a colorless oil (8.95 g, yield: 73.2%). 1H NMR (CDCl3, 400 MHz): δ 1.41 (s, 6H), 2.51 (s, 2H), 2.98 (s, 2 H). LRMS (ESI+) for C14H22N2O2 (250.2); Found: 251 (MH+).

Workup

  1. waitThe reaction was left
  2. customThe solvent was removed
  3. additionthe residue was taken up in a mixture of ethyl acetate (300 mL) and water (100 mL)
  4. customThe layers were separated
  5. extractionthe organic layer extracted with water (2×100 mL)
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to an oil
  9. customThe crude oil was purified on an ISCO purification system with gradient elution from 2% methanol in DCM to 30% methanol in DCM
  10. customThe desired fraction was collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-e577f3e537be4b1d87e42f0b9ee1f4c6
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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