p-Toluenesulfonic acid → N-(5-Hydroxypentyl)-N-isopropylheptanamide

HRID 1485824Notes

Reaction equation

HRID 1485824 reaction equation
[Si]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]([CH:33]([CH3:35])[CH3:34])[C:25](=[O:32])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]([CH:33]([CH3:34])[CH3:35])[C:25](=[O:32])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 70819093N-(5-(tert-Butyldiphenylsilyloxy)pentyl)-N-isopropylheptanamide

Product 1

HCID 86716479N-(5-Hydroxypentyl)-N-isopropylheptanamideYield 101.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5 (4.75 g, 9.02 mmol) and p-toluenesulfonic acid in MeOH (50 mL) was stirred at rt for 12 h, then quenched with solid NaHCO3 and filtered. The filtrate was evaporated under vacuum and the residue was dissolved in ethyl acetate (50 mL). The ethyl acetate layer was washed with water (2×50 mL), brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography using 50-60% ethyl acetate/hexane as eluent to afford alcohol 6 (2.35 g, 93%) as a colorless, viscous liquid. TLC:EtOAc/hexanes (1:1), Rf˜0.30; 1H NMR (400 MHz, 55/45 mixture of rotamers) δ 4.58-4.66 and 3.96-4.08 (m, 1H, rotamers), 3.56 and 3.70 (t, J=5.4 Hz, 2H, rotamers), 3.02 and 3.16 (t, J=5.2 Hz, 2H, rotamers), 2.38 and 2.26 (t, J=6.3 Hz, 2H, rotamers), 1.50-1.64 (m, 6H), 1.22-1.40 (m, 8H), 1.13 and 1.09 (d, J=7.5 Hz, 6H, rotamers), 0.84 (t, J=7.3 Hz, 3H); 13C NMR (100 MHz, 55/45 mixture of rotamers) δ 172.81, 62.66, 62.60, 48.41, 45.55, 43.56, 41.04, 34.08, 34.0, 32.46, 32.43, 31.86, 31.57, 29.40, 25.87, 25.70, 23.77, 23.73, 22.75, 21.57, 20.72, 14.26.

Workup

  1. customquenched with solid NaHCO3
  2. filtrationfiltered
  3. customThe filtrate was evaporated under vacuum
  4. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
  5. washThe ethyl acetate layer was washed with water (2×50 mL), brine (50 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-a4d38c7ba0d4477cb49e6d269b459839
Source dataset
uspto-grants-2016_08
Patent number
US09422318B2

Reaction notes

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