HCID 67155628, compound → HCID 44481362, compound

HRID 452404Notes

Reaction equation

HRID 452404 reaction equation
[CH2:1]([N:8](C)[CH2:9][CH:10]1[O:15][C:14]2[CH:16]=[C:17]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:18]=[CH:19][C:13]=2[CH2:12][O:11]1)C1C=CC=CC=1>[Pd].CCO>[CH3:1][NH:8][CH2:9][CH:10]1[O:15][C:14]2[CH:16]=[C:17]([S:20]([CH3:23])(=[O:21])=[O:22])[CH:18]=[CH:19][C:13]=2[CH2:12][O:11]1

Participants

4

Reactant 1

HCID 67155628HCID 67155628, compound

Product 1

HCID 44481362HCID 44481362, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(−)-N-benzyl-N-methyl-1-[7-(methylsulfonyl)-4H-1,3-benzodioxin-2-yl]methanamine (0.37 g, 1.06 mmol), palladium on carbon (10%, 45 mg) and EtOH (15 ml) was hydrogenated at 45 psi for 14 h. The reaction mixture was filtered through a pad of celite and the filtrate was evaporated to dryness (0.25 g). Purification by flash chromatography (EtOAc/MeOH 2:1) afforded the pure title compound (0.23 g, 84%, >95% e.e.). The amine was converted into the hydrochloric acid salt and crystallized from EtOH/MeOH/DEE. M.p. 225° C. [α]DMeOH=−81°. MS m/z (rel. intensity, 70 eV) 257 (M+, 2), 123 (bp), 106 (29), 77 (88), 51 (61).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. customthe filtrate was evaporated to dryness (0.25 g)
  3. customPurification by flash chromatography (EtOAc/MeOH 2:1)

Sources & evidence

ORD record
ord-bc2c7e32e0e14fd6867acd898356e4aa
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

Loading…