p-Toluenesulfonic acid → (R)-1-((2R,5R)-5-methyl-tetrahydro-furan-2-yl)-propylamine para-toluenesulfonate salt

HRID 1024569Notes

Reaction equation

HRID 1024569 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C@H:11]1[CH2:15][CH2:14][C@@H:13]([CH3:16])[O:12]1)[CH2:9][CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31]([OH:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1>C(Cl)Cl.CCOC(C)=O>[C:25]1([CH3:35])[CH:26]=[CH:27][C:28]([S:31]([OH:34])(=[O:32])=[O:33])=[CH:29][CH:30]=1.[CH3:16][C@H:13]1[O:12][C@@H:11]([C@H:8]([NH2:7])[CH2:9][CH3:10])[CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6422Trifluoroacetic acidHCID 67083657[(R)-1-(2R,5R)-(5-methyl-tetrahydro-furan-2-yl)-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 86638630(R)-1-((2R,5R)-5-methyl-tetrahydro-furan-2-yl)-propylamine para-toluenesulfonate salt

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an ice-cooled solution of [(R)-1-(2R,5R)-(5-methyl-tetrahydro-furan-2-yl)-propyl]-carbamic acid tert-butyl ester (416 mg, 1.71 mmol) in dry DCM (4 ml) was added TFA (200 μl, 1.41 mmol) under an inert atmosphere of nitrogen. After stirring at room temperature for 3 h, the mixture was diluted with EtOAc (15 ml) and washed with saturated aqueous Na2CO3. The organic portion was dried (Na2SO4) and then para-toluenesulfonic acid (147 mg, 0.77 mmol) was added. After stirring, the solvent was removed in vacuo and recrystallisation from MeCN affords the title compound as a white solid. 1H NMR (DMSO) 0.90 (3H, t, CH3), 1.20 (3H, d, CH3), 1.45 (2H, m, 2×CH), 1.59 (1H, m, CH), 1.65 (1H, m, CH), 1.95 (2H, m, CH2), 2.30 (3H, s, CH3), 2.93 (1H, m, CH), 3.75 (1H, dd, CH), 3.95 (1H, m, CH), 7.10 (2H, d, 2×CH), 7.48 (2H, d, 2×CH), 7.75 (3H, s, NH3+).

Workup

  1. washwashed with saturated aqueous Na2CO3
  2. dry with materialThe organic portion was dried (Na2SO4)
  3. stirringAfter stirring
  4. customthe solvent was removed in vacuo and recrystallisation from MeCN

Sources & evidence

ORD record
ord-9e8f06aca6c0457fae3a9e33aadcd559
Source dataset
uspto-grants-2014_05
Patent number
US08722925B2

Reaction notes

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