HCID 67155628, compound → HCID 44481362, compound

HRID 452405Notes

Reaction equation

HRID 452405 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 89%

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 (20 ml) was hydrogenated at 45 psi for 14 h. Purification by flash chromatography (EtOAc/MeOH 2:1) afforded the pure title compound (0.24 g, 89%, >95% e.e.). The amine was converted into the hydrochloric acid salt and crystallized from EtOH/MeOH/DEE. M.p. 224° C. [α]DMeOH=+77°. 1H-NMR (400 MHz, MeOH): δ 7.48 (1h, dd, J1 8.0 Hz, J2 1.6 Hz), δ 7.43 (1H, d, J 2.0 Hz), δ 7.18 (1H, d, J 8.0 Hz), δ 5.19 (1H, t, J 4.8 Hz), δ 5.00 (2H, dd, J 50 Hz, J2 16 Hz), δ 3.03 (3H, s), δ 2.99 (2H, d, J 4.0 Hz), δ 2.53 (3H, s), δ 1.54 (1H, s).

Workup

  1. customPurification by flash chromatography (EtOAc/MeOH 2:1)

Sources & evidence

ORD record
ord-3b0221aa3e1a418a9587b761bf8d353d
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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