Benzyl succinimido carbonate → HCID 60134584, compound

HRID 2061081Notes

Reaction equation

HRID 2061081 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]([CH3:13])([NH2:12])[CH3:11])[CH2:4][CH2:3]1.[C:15](ON1C(=O)CCC1=O)([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>C1COCC1>[CH3:1][C:2]1([CH3:14])[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][C:10]([NH:12][C:15](=[O:16])[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([CH3:13])[CH3:11])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 64679948HCID 64679948, compound

Product 1

HCID 60134584HCID 60134584, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Crude 4-(4,4-dimethylpiperidin-1-yl)-2-methylbutan-2-amine (5.80 g, 29.2 mmol) was dissolved into THF (100 mL). To this solution was added CbzOSu (7.29 g, 1 equiv, 29.2 mmol) in one portion. The reaction was left to stir at room temperature for 3 d. The solvent was removed and the residue was taken up in a mixture of diethyl ether (150 mL) and water (50 mL). The layers were separated and the organic layer washed with 1 M sodium carbonate (2×50 mL), 1M HCl (50 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 10-80% ethyl acetate in hexanes. The desired fractions were collected and concentrated to give a white solid (4.75 g, yield: 49.0%). 1H NMR (CDCl3, 400 MHz): δ 0.92 (s, 6H), 1.35-1.40 (bm, 10H), 1.58-1.63 (t, J=10.8, 2 H), 2.40 (bs, 4H), 2.44-2.52 (t, J=10.8, 2H), 5.03 (s, 2H), 7.27-38 (m, 5H). LRMS (ESI+) for C20H32N2O2 (332.2); Found: 333 (MH+).

Workup

  1. waitThe reaction was left
  2. customThe solvent was removed
  3. additionthe residue was taken up in a mixture of diethyl ether (150 mL) and water (50 mL)
  4. customThe layers were separated
  5. washthe organic layer washed with 1 M sodium carbonate (2×50 mL), 1M HCl (50 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 10-80% ethyl acetate in hexanes
  10. customThe desired fractions were collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-a161b2f2edcc46bfb148d65e0253a818
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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