2-Chlorobenzothiazole → (3S)-1-(1,3-benzothiazol-2-yl)-4,4-dimethyl-3-pyrrolidinol

HRID 750399Notes

Reaction equation

Cl.[CH3:2][C:3]1([CH3:9])[CH2:7][NH:6][CH2:5][C@H:4]1[OH:8].Cl[C:11]1[S:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1.C(=O)(O)[O-].[Na+]>O>[S:12]1[C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=[C:11]1[N:6]1[CH2:7][C:3]([CH3:9])([CH3:2])[C@H:4]([OH:8])[CH2:5]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a slurry of 600 mg (4 mmol) of (3S)-4,4-dimethyl-3-pyrrolidinol hydrochloride and 670 mg (4 mmol) of 2-chlorobenzthiazole was added a solution of 1.0 g (12 mmol) of sodium bicarbonate in water. The reaction mixture was stirred at 80° C. overnight, diluted with water, and extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated under reduced pressure to afford 950 mg (96%) of (3S)-1-(1,3-benzothiazol-2-yl)-4,4-dimethyl-3-pyrrolidinol. 1H NMR (300 MHz, DMSO-d6) δ 7.72 (d, J=8 Hz, 1H), 7.41 (d, J=8 Hz, 1H), 7.23 (t, J=7 Hz, 1H), 7.00 (t, J=7 Hz, 1H), 5.23 (d, J=5 Hz, 1H), 3.84 (m, 1H), 3.77 (m, 1H), 3.38-3.21 (m, 3H) 1.02 (s 3H), 1.00 (s, 3H). Cl-LCMS m/z 249 (M+H).

Workup

extractionextracted with ethyl acetate
dry with materialThe extract was dried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-55e4f0f28d164fca9a09acee47354a83
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07402606B2

Reaction notes

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