Pyrrolidine → HCID 44469455, compound

HRID 38903Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of [7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.4 g, 0.9 mmol), pyrrolidine (1 ml) and ACN (3 ml) was heated under microwave radiation at 120° C. for 20 min. Purification on SCX-3 column (TEA/MeOH) and twice on flash column chromatography (Isooctane/EtOAc/MeOH). Yield: 0.2 g, 75%. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 221° C. MS m/z (rel. intensity, 70 eV) 297 (M+, 1), 85 (6), 84 (bp), 79 (2), 55 (4).

Workup

customPurification on SCX-3 column (TEA/MeOH)
customcrystallized from MeOH/Et2O

Sources & evidence

ORD record: ord-06f1855b5e26442d8dd650b36086854b
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524766B2

Reaction notes

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