Tetrahydrofuran → HCID 60134460, compound

HRID 2061086Notes

Reaction equation

HRID 2061086 reaction equation
C(=O)([O-])O.[Na+].[CH:6]1([N:12]([CH3:19])[CH2:13][CH2:14][C:15]([CH3:18])([NH2:17])[CH3:16])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C1COCC1.[C:25](ON1C(=O)CCC1=O)([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>O>[CH:6]1([N:12]([CH3:19])[CH2:13][CH2:14][C:15]([NH:17][C:25](=[O:26])[O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([CH3:16])[CH3:18])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 83172Benzyl succinimido carbonateHCID 516892Sodium BicarbonateHCID 64678886HCID 64678886, compound

Product 1

HCID 60134460HCID 60134460, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydrogen carbonate (15.0 g, 0.18 mol) dissolved in water (200 mL) was added to reaction containing crude N1-cyclohexyl-N1,3-dimethylbutane-1,3-diamine (14.0 g, 46.1 mmol) was dissolved into THF (200 mL). CbzOSu (11.0 g, 1 equiv, 44.2 mmol) was added in one portion to the reaction and left to stir at room temperature for 16 h. The organic solvent was removed and the aqueous residue was extracted with DCM (3×150 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated to a pale yellow oil (12.7 g). The crude oil was purified on an ISCO purification system with gradient elution from 20-100% ethyl acetate then1-10% methanol in ethyl acetate. The desired fraction was collected and concentrated to give a colorless oil (5.27 g, yield: 34.4%). 1H NMR (CDCl3, 400 MHz): δ 1.0-1.49 (m, 5H), 1.37 (s, 6H), 1.55 (t, 2H), 1.6-1.64 (m, 1H), 1.76 (bs, 4H), 2.21 (s, 3H), 2.32-2.4 (m, 1H), 2.60 (t, 2H), 5.03 (s, 2H), 7.2-7.4 (m, 5H), 7.96 (s, 1H). LRMS (ESI+) for C20H32N2O2 (332.3); Found: 333 (MH+).

Workup

  1. additionwas added to reaction
  2. waitleft
  3. customThe organic solvent was removed
  4. extractionthe aqueous residue was extracted with DCM (3×150 mL)
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to a pale yellow oil (12.7 g)
  8. customThe crude oil was purified on an ISCO purification system with gradient elution from 20-100% ethyl acetate then1-10% methanol in ethyl acetate
  9. customThe desired fraction was collected
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-7b3cd96b696c40ca8b1a729b45e2a890
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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