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

HRID 38961

Reaktionsgleichung

Reaktionsgleichung von HRID 38961
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:18][C:17]3[CH:19]=[C:20]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[CH3:27][C:28]([CH3:32])([CH3:31])[CH2:29][NH2:30]>C(#N)C>[CH3:27][C:28]([CH3:32])([CH3:31])[CH2:29][NH:30][CH2:12][C@@H:13]1[O:18][C:17]2[CH:19]=[C:20]([S:23]([CH3:26])(=[O:24])=[O:25])[CH:21]=[CH:22][C:16]=2[O:15][CH2:14]1

Komponenten

4

Edukt 2

HCID 79882NeopentylamineHCID 86652935[(2R)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

Produkt 1

HCID 444683782,2-Dimethyl-N-{[(2S)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methyl}propan-1-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

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).

Aufarbeitung

  1. customPurification on SCX-3 column (TEA/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-dcb28ffeacdd4c8caf68a4dc4a48c49a
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524766B2

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