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

HRID 38906Notes

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.[CH3:27][CH:28]([CH3:31])[CH2:29][NH2:30]>C(#N)C>[CH3:27][CH:28]([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

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of [(2R)-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.19 g, 0.48 mmol), 2-methylpropane-1-amine (0.9 ml) and ACN (3 ml) was heated under microwave radiation at 120° C. for 20 min. Purification on SCX-3 column (TEA/MeOH) and flash column chromatography (DCM/MeOH). Yield: 0.11 g, 74%. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 214° C. MS m/z (rel. intensity, 70 eV) 299 (M+, 6), 86 (100), 256 (21), 57 (8), 70 (6). [α]=−58° (MeOH).

Workup

customPurification on SCX-3 column (TEA/MeOH) and flash column chromatography (DCM/MeOH)
customcrystallized from MeOH/Et2O
custom[α]=−58° (MeOH)

Sources & evidence

ORD record: ord-cfbb3531158c48fc852fede59e0efdef
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524766B2

Reaction notes

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