Neopentylamine → 2,2-Dimethyl-N-{[(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methyl}propan-1-amine

Participants

Role	Name	HCID	Charge
Reactant	Neopentylamine	HCID 79882	—
Reactant	[(2R)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate	HCID 86652935	—
Solvent	Acetonitrile	HCID 6342	—
Product	2,2-Dimethyl-N-{[(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methyl}propan-1-amine	HCID 44468378	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of [(2R)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.196 g, 0.5 mmol), 2,2-dimethylpropan-1-amine (1 ml, 8.5 mmol) and ACN (3 ml) was heated under microwave radiation at 120° C. for 20 min. Purification on SCX-3 column (TEA/MeOH) and by flash chromatography (EtOAc) gave the title compound. Yield: 0.1 g. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 242° C. MS m/z (rel. intensity, 70 eV) 313 (M+, 6), 298 (32), 257 (14), 256 (bp), 207 (12), 100 (92). [α]=−53° (MeOH).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08524766B2
Source dataset	uspto-grants-2013_09
ORD ID	ord-dcb28ffeacdd4c8caf68a4dc4a48c49a
Source note	uspto-grants-2013_09