Benzyl succinimido carbonate → HCID 60134496, compound

HRID 2061090Notes

Reaction equation

HRID 2061090 reaction equation
[CH3:1][C:2]([NH2:11])([CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)[CH3:3].[C:12](ON1C(=O)CCC1=O)([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]>C1COCC1>[CH3:3][C:2]([NH:11][C:12](=[O:13])[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1)[CH3:1]

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 595112471226914-25-5

Product 1

HCID 60134496HCID 60134496, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Crude 2-methyl-4-(pyrrolidin-1-yl)butan-2-amine (5.70 g, 31.7 mmol) was dissolved into THF (200 mL). To this solution was added CbzOSu (7.92 g, 1 equiv, 31.7 mmol) 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), 1 M HCl (50 mL) and brine (50 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated to a pale yellow oil (9.0 g). The crude oil was purified on an ISCO purification system with gradient elution from 5-90% ethyl acetate in hexanes. The desired fraction was collected and concentrated to give a pale yellow oil (5.76 g, yield: 62.5%). 1H NMR (CDCl3, 400 MHz): δ 1.34 (s, 6H), 1.76-1.84 (m, 6H), 2.58-2.66 (m, 6H), 5.04 (s, 2H), 6.36 (bs, 1H), 7.27-7.39 (m, 5H). LRMS (ESI+) for C17H26N2O2 (290.2); Found: 291 (MH+).

Workup

  1. waitThe reaction was left
  2. customThe solvent was removed
  3. additionthe residue was taken up in a mixture of ethyl acetate (150 mL) and water (50 mL)
  4. customThe layers were separated
  5. washthe organic layer washed with 1 M sodium carbonate (2×50 mL), 1 M HCl (50 mL) and brine (50 mL)
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to a pale yellow oil (9.0 g)
  9. customThe crude oil was purified on an ISCO purification system with gradient elution from 5-90% ethyl acetate in hexanes
  10. customThe desired fraction was collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-0c28209f6c344dc4ba0d7398237bbee8
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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