Ethylamine → N-{[(2S)-7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methyl}ethanamine

HRID 38897Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of [(2R)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (1.0 g, 2.51 mmol), ethanamine (2 ml, 70% in water) and ACN (6 ml) was heated under microwave radiation at 120° C. for 20 min. Purification on SCX-3 column (TEA/MeOH) and flash column chromatography (Isooctane/EtOAc/MeOH). Yield: 0.53 g, 78%. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 271° C. MS m/z (rel. intensity, 70 eV) 271 (M+, 29), 58 (100), 59 (10), 272 (7), 79 (5). [α]=−66° (MeOH).

Workup

customPurification on SCX-3 column (TEA/MeOH) and flash column chromatography (Isooctane/EtOAc/MeOH)
customcrystallized from MeOH/Et2O
custom[α]=−66° (MeOH)

Sources & evidence

ORD record: ord-e4934b19b2bd48b7bd8265b719dcc552
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524766B2

Reaction notes

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