Benzyl succinimido carbonate → HCID 60134471, compound

HRID 2061052Notes

Reaction equation

HRID 2061052 reaction equation
[CH3:1][C:2]([NH2:12])([CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH3:3].[C:13](ON1C(=O)CCC1=O)([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>C1COCC1>[CH3:3][C:2]([NH:12][C:13](=[O:14])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)[CH3:1]

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 64679077HCID 64679077, compound

Product 1

HCID 60134471HCID 60134471, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude 2-methyl-4-(piperidin-1-yl)butan-2-amine in THF (100 mL) was added CbzOSu (8.10 g, 1.2 equiv, 33.2 mmol) in one portion. The reaction mixture was left to stir at room temperature for 17 h. The solvent was removed under reduced pressure 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 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 5% ethyl acetate in hexanes to 100% ethyl acetate. The desired fractions were collected and concentrated to give a pale yellow oil (4.91 g, 49.6%). 1H NMR (CDCl3, 400 MHz): δ 1.36 (s, 6H), 1.37-1.45 (m, 2H), 1.51-1.53 (m, 6H), 2.30-2.45 (m, 6H), 2.38 (s, 2H), 5.05 (s, 2H), 7.27-7.36 (m, 5H). LRMS (ESI+) for C18H28N2O2 (304.2); Found: 305 (MH+).

Workup

  1. waitThe reaction mixture was left
  2. customThe solvent was removed under reduced pressure
  3. additionthe residue was taken up in a mixture of ethyl acetate (300 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 5% ethyl acetate in hexanes to 100% ethyl acetate
  10. customThe desired fractions were collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-731bc837048e4cf88c7ef524e13a0bb2
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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