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

HRID 1182299Notes

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 heated to 80° C. and stirred overnight. It was then diluted with water, the resulting mixture was extracted with ethyl acetate. The extracts were combined, dried over anhydrous 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-6): δ 7.76 (d, J=8 Hz, 1H), 7.46 (d, J=8 Hz, 1H), 7.27 (t, J=8 Hz, 1H), 7.04 (t, J=8 Hz, 1H), 5.27 (d, J=5 Hz, 1H), 3.84–3.77 (m, 2H), 3.39–3.25 under DMSO peak (m, 3H), 1.05 (d, J=8 Hz, 6H); ES-LCMS m/z 249 (M+H).

Workup

extractionthe resulting mixture was extracted with ethyl acetate
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-5a7745a668df466396981e74ae5da58d
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07288541B2

Reaction notes

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