Reaction #67183

ord-58e9af68174749a1acec1e6a4f9d36f0

Reaction equation

Cc1ccc(S(=O)(=O)OC[C@@H]2COc3ccc(S(C)(=O)=O)cc3O2)cc1
[(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate
CC(C)CN
2-methylpropane-1-amine
→
CC(C)CNC[C@@H]1COc2ccc(S(C)(=O)=O)cc2O1
2-METHYL-N-{[(2R)-7-(METHYLSULFONYL)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]METHYL}PROPAN-1-AMINE

Reactants

Cc1ccc(S(=O)(=O)OC[C@@H]2COc3ccc(S(C)(=O)=O)cc3O2)cc1
[(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate
CC(C)CN
2-methylpropane-1-amine

Reagents

None

Solvents

CC#N
ACN

Conditions

Temperature
120°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherPurification on SCX-3 column (TEA/MeOH) and flash column chromatography (EtOAc/MeOH)
  2. 2
    Othercrystallized from MeOH/Et2O
  3. 3
    Other[α]=+65° (MeOH)

Procedure

A mixture of [(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.2 g, 0.5 mmol), 2-methylpropane-1-amine (1 ml) and ACN (2 ml) was heated under microwave radiation at 120° C. for 30 min. Purification on SCX-3 column (TEA/MeOH) and flash column chromatography (EtOAc/MeOH). Yield: 0.1 g, 77%. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 213° C. MS m/z (rel. intensity, 70 eV) 299 (M+, 4), 256 (16), 207 (11), 86 (bp), 57 (8). [α]=+65° (MeOH).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08524766B2uspto-grants-2013_09